Novel herbicides

ABSTRACT

Pyrandione, thiopyrandione and cyclohexanetrione compounds of formula (I), which are suitable for use as herbicides.

The present invention relates to novel, herbicidally active cyclicdiones, and derivatives thereof, to processes for their preparation, tocompositions comprising those compounds, and to their use in controllingweeds, especially in crops of useful plants such as rice, corn, cereals,cotton, soya, sugarbeet, oilseed rape or canola, sugar cane, or ininhibiting plant growth.

Cyclic diones having herbicidal action are described, for example, in WO01/74770.

Novel pyrandione, thiopyrandione and cyclohexanetrione compounds havingherbicidal and growth-inhibiting properties have now been found.

The present invention accordingly relates to compounds of formula I

whereinR¹, R², R³ and R⁴, independently of each other, are hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₄ alkyl,C₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄alkylsulfinylC₁-C₄alkyl,C₁-C₄alkylsulfonylC₁-C₄alkyl, cyclopropyl or cyclopropyl substituted byC₁- or C₂alkyl, C₁- or C₂ haloalkyl or halogen; cyclobutyl or cyclobutylsubstituted by C₁- or C₂ alkyl; oxetanyl or oxetanyl substituted by C₁-or C₂ alkyl; C₅-C₇cycloalkyl or C₅-C₇cycloalkyl substituted by C₁- orC₂alkyl or C₁- or C₂haloalkyl, where a methylene group of the cycloalkylmoiety is optionally replaced by an oxygen or sulfur atom or a sulfinylor sulfonyl group; C₄-C₇cycloalkenyl or C₄-C₇cycloalkenyl substituted byC₁- or C₂alkyl or C₁- or C₂haloalkyl, where a methylene group of thecycloalkenyl moiety is optionally replaced by an oxygen or sulfur atomor a sulfinyl or sulfonyl group; cyclopropylC₁-C₅alkyl orcyclopropylC₁-C₅alkyl substituted by C₁- or C₂alkyl, C₁- or C₂haloalkylor halogen; cyclobutylC₁-C₅alkyl or cyclobutylC₁-C₅alkyl substituted byC₁-C₂ alkyl; oxetanylC₁-C₅alkyl or oxetanylC₁-C₅alkyl substituted by C₁-or C₂alkyl; C₅-C₇cycloalkylC₁-C₅alkyl or C₅-C₇cycloalkylC₁-C₅alkylsubstituted by C₁- or C₂alkyl or C₁- or C₂haloalkyl, where a methylenegroup of the cycloalkyl moiety is optionally replaced by an oxygen orsulfur atom or a sulfinyl or sulfonyl group; C₄-C₇cycloalkenylC₁-C₅alkylor C₄-C₇cycloalkenylC₁-C₅alkyl which is substituted by C₁- or C₂alkyl orC₁- or C₂haloalkyl, where a methylene group of the cycloalkenyl moietyis optionally replaced by an oxygen or sulfur atom or a sulfinyl orsulfonyl group; phenyl or phenyl substituted by C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄haloalkyl, halogen, nitro, cyano, C₁-C₄ alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or C₁-C₄alkylcarbonyl; benzyl orbenzyl substituted by C₁-C₄alkyl, C₁-C₄ alkoxy, C₁-C₄haloalkyl, halogen,nitro, cyano, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl orC₁-C₄alkylcarbonyl; heteroaryl or heteroaryl substituted by C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄haloalkyl, halogen, nitro, cyano, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or C₁-C₄alkylcarbonyl; orR¹ and R², or R³ and R⁴, are joined to form a 3-7 membered saturatedring in which a methylene group is optionally replaced by an oxygen orsulfur atom, and which may be optionally substituted by C₁- or C₂-alkyl,halogen or C₁-C₂ alkoxy, or a 5-7 membered unsaturated ring in which amethylene group is optionally replaced by an oxygen or sulfur atom, andwhich may be optionally substituted by C₁- or C₂-alkyl, halogen or C₁-C₂alkoxy; orR¹ and R³ are joined to form a 5-7 membered saturated or unsaturatedring or a 5-7 membered saturated or unsaturated ring optionallysubstituted by C₁- or C₂alkyl, C₁- or C₂alkoxy, hydroxy or halogen;Y is O, C═O, S(O)_(m) or S(O)_(n)NR⁵; provided that when Y is C═O, R³and R⁴ are different from hydrogen when either R¹ or R² is hydrogen, andR¹ and R² are different from hydrogen when either R³ or R⁴ is hydrogen;m is 0 or 1 or 2 and n is 0 or 1;R⁵ is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxycarbonyl,tri(C₁-C₆alkyl)silyl-ethyloxycarbonyl, C₁-C₆haloalkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆cycloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byR⁶; benzylcarbonyl or benzylcarbonyl substituted by R⁶; pyridylcarbonylor pyridylcarbonyl substituted by R⁶; phenoxycarbonyl or phenoxycarbonylsubstituted by R⁶; benzyloxycarbonyl or benzyloxycarbonyl substituted byR⁶;R⁶ is C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl,carboxyl or halogen;Het is a an optionally substituted monocyclic or bicyclic heteroaromaticring; andG is hydrogen, an alkali metal, alkaline earth metal, sulfonium,ammonium or a latentiating group.

In the substituent definitions of the compounds of the formula I, thealkyl substituents and alkyl moieties of alkoxy, alkylamino etc. having1 to 6 carbon atoms are preferably methyl, ethyl, propyl, butyl, pentyland hexyl, in the form of their straight and branched isomers. Thealkenyl and alkynyl radicals having 2 to 6 carbon atoms as well as up to10 carbon atoms can be straight or branched and can contain more than 1double or triple bond. Examples are vinyl, allyl, propargyl, butenyl,butynyl, pentenyl and pentynyl. Suitable cycloalkyl groups contain 3 to7 carbon atoms and are for example cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl and cycloheptyl. Cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl are preferred. Heterocycles, as a rule, correspond to thecarbocycles or cycloalkyl radicals mentioned above with the exceptionthat one or two methylene groups are replaced by an oxygen, sulphur ornitrogen atom, which can be substituted further. Preferred halogens arefluorine, chlorine and bromine. Preferred examples of heteroaryls R¹,R², R³, R⁴, R⁸ and R¹² are thienyl, furyl, pyrrolyl, isoxazolyl,oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, triazolyl,tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazolyl,thiadiazolyl and pyridazinyl, and, where appropriate, N-oxides and saltsthereof. These heteroaryls can be substituted by one or moresubstituents, where preferred substituents are, for example, halogen,C₁-C₄ alkyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, polyC₁-C₄ alkox C₁-C₄ yalkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, nitro, cyano,C₂-C₄alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, aryl, aryl substitutedby C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy, cyanoor nitro, or heteroaryl or heteroaryl substituted by C₁-C₂-alkyl,C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy, cyano or nitro.

The group G denotes hydrogen, an alkali metal cation, alkaline earthmetal cation, sulfonium cation (preferably —S(C₁-C₆alkyl₃)⁺) or ammoniumcation (preferably —NH₄ ⁺ or —N(C₁-C₆alkyl)₄ ⁺), or a latentiatinggroup. These latentiating groups G are selected to allow its removal byone or a combination of biochemical, chemical or physical processes toafford compounds of formula I where G is H before, during or followingapplication to the treated area or plants. Examples of these processesinclude enzymatic cleavage, chemical hydrolysis and photoloysis.Compounds bearing such latentiating groups G may offer certainadvantages, such as improved penetration of the cuticula of the plantstreated, increased tolerance of crops, improved compatibility orstability in formulated mixtures containing other herbicides, herbicidesafeners, plant growth regulators, fungicides or insecticides, orreduced leaching in soils. The latentiating group G is preferablyselected from the groups G is C₁-C₈ alkyl, C₂-C₈ haloalkyl,phenylC₁-C₈alkyl (wherein the phenyl may optionally be substituted byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyanoor by nitro), heteroarylC₁-C₈alkyl (wherein the heteroaryl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano or by nitro), C₃-C₈ alkenyl, C₃-C₈haloalkenyl, C₃-C₈ alkynyl, C(X^(a))—R^(a), C(X^(b))—X^(c)—R^(b),C(X^(d))—N(R^(c))—R^(d), —SO₂—R^(e), —P(X^(e))(R^(f))—R^(g) orCH₂—X^(f)—R^(h) wherein X^(a), X^(b), X^(c), X^(d), X^(e) and X^(f) areindependently of each other oxygen or sulfur;

R^(a) is H, C₁-C₁₈alkyl, C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₁-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀-aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₈-trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl, (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, R^(b) isC₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₃-C₁₈alkynyl, C₂-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₂-C₁₀-aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsuffinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl, (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₃-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, R^(c) and R^(d)are each independently of each other hydrogen, C₁-C₁₀alkyl,C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₂-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl,C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl,C₂-C_(o)dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl,C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl,C₃-C₅alkynyloxyC₁-C₅alkyl, C₁-C₅alkylthioC₁-C₅alkyl,C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl,C₂-C_(o)alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl,C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl,C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C_(o)dialkylaminocarbonylC₁-C₅alkyl,C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₂-C₅alkylaminoalkyl,C₃-C₆-trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl, (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, heteroarylaminoor heteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, diheteroarylaminoor diheteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, phenylamino orphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or by nitro, diphenylamino ordiphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or by nitro, amino, C₁-C₃alkylamino,C₁-C₃dialkylamino, C₁-C₃alkoxy or C₃-C₇cycloalkylamino,di-C₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy or R^(c) and R^(d) may jointogether to form a 3-7 membered ring, optionally containing oneheteroatom selected from O or S and optionally substituted by 1 or 2C₁-C₃alkyl groups. R^(e) is C₁-C₁₀alkyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl,C₁-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₅dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₆-trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano, amino or by nitro,heteroarylamino or heteroarylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or bynitro, diheteroarylamino or diheteroarylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano ornitro, phenylamino or phenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano, nitro,amino, diphenylamino, or diphenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,or C₃-C₇cycloalkylamino, diC₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy,C₁-C₁₀alkoxy, C₁-C₁₀haloalkoxy, C₁-C₅alkylamino or C₂-C₈dialkylamino,R^(f) and R⁹ are each independently of each other C₁-C₁₀alkyl,C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₁-C₁₀alkoxy, C₁-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₂-C₅alkylaminoalkyl,C₃-C₆-trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro,heteroarylamino or heteroarylamino substituted by C₁-C₃ alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or bynitro, diheteroarylamino or diheteroarylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,phenylamino or phenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, amino, hydroxyl,diphenylamino, or diphenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,or C₃-C₇cycloalkylamino, diC₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy,C₁-C₁₀haloalkoxy, C₁-C₅alkylamino or C₂-C₈dialkylamino, benzyloxy orphenoxy, wherein the benzyl and phenyl groups may in turn be substitutedby C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro, and R^(h) is C₁-C₁₀alkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl,C₁-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₂-C₁₈-aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano or by nitro), heteroarylC₁-C₅alkyl(wherein the heteroaryl may optionally be substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro),phenoxyC₁-C₅alkyl (wherein the phenyl may optionally be substituted byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyanoor by nitro), heteroaryloxyC₁-C₅alkyl (wherein the heteroaryl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano or by nitro), C₃-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen or by nitro, orheteroaryl, or heteroaryl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro.

Preferably, G denotes C(X^(a))—R^(a) or C(X^(b))—X^(c)—R^(b), and themeanings of X^(a), R^(a), X^(b), X^(c) and R^(b) are as defined above.More important groups G comprise hydrogen, an alkali metal or alkalineearth metal, where hydrogen is particularly preferred.

In a preferred group of compounds of the formula I, R¹, R², R³ and R⁴,independently of each other, are hydrogen, C₁-C₄ alkyl, in particularhydrogen, methyl or ethyl, and most preferably methyl.

In another preferred group of compounds of the formula I, R¹ and R³ arejoined to form a 5-7 membered saturated or unsaturated ring or a 5-7membered saturated or unsaturated ring substituted by C₁- or C₂alkyl,C₁- or C₂alkoxy or halogen and wherein R² and R⁴, independently of eachother, are hydrogen, methyl or ethyl.

Preferred meanings of Y are O, C═O and S.

Het is preferably an optionally substituted monocyclic 5- or 6-memberednitrogen or sulfur containing heteroaryl.

More preferably, Het is a group of the formula R₁ to R₁₂

wherein A designates the point of attachment to the ketoenol moiety, and

W¹ is N or CR¹⁰;

W² and W³ are independently of each other N or CR⁸;

W⁴ is N or CR¹¹;

with the proviso that at least one of W¹, W², W³ or W⁴ is N;

X is O, S, Se, or NR¹³; Z is N or CR¹⁴;

R⁷ is halogen, C₁-C₄ alkyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,nitro or cyano;R⁸ is hydrogen, halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₁-C₄alkoxy, C₂-C₄ alkenyloxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulphinyl, C₁-C₄alkylsulphonyl, C₁-C₄ alkoxy C₁-C₄ alkyl, poly C₁-C₄ alkoxyC₁-C₄ alkyl,C₁-C₄ alkylthio C₁-C₄ alkyl, each of which is unsubstituted orsubstituted by halogen, C₃-C₈cycloalkyl, thienyl, furyl, pyrrolyl,isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl,triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl,oxadiazolyl, thiadiazolyl, pyridazinyl, quinolinyl, isoquinolinyl,cinnolinyl, quinazolinyl and quinoxalinyl, N-oxides and salts thereof,each of these substituents being unsubstituted or substituted byhalogen, C₁-C₄ alkyl, haloC₁-C₄ alkyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulphinyl, C₁-C₄ alkyl-sulphonyl, haloC₁-C₄alkyl, haloC₁-C₄ alkoxy, cyano or nitro;R⁹ is hydrogen, C₁-C₄ alkyl, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₄ haloalkylor C₂-C₃ haloalkenyl;R¹⁰ is hydrogen, methyl, halomethyl or halogen;R¹¹ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl,C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl or cyano;R¹² is hydrogen, methyl, ethyl, halomethyl, haloethyl, aryl, arylsubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂haloalkoxy, cyano or nitro, heteroaryl or heteroaryl substituted byC₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy, cyano ornitro;R¹³ is hydrogen, methyl or halomethyl; andR¹⁴ is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano ornitro.

In particular, Het is a group of the formula R₂, wherein X is sulfur, R⁸is thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl,thiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridyl,pyrimidinyl, pyrazinyl, triazinyl, oxadiazolyl, thiadiazolyl,pyridazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl andquinoxalinyl, N-oxides and salts thereof, each of which is optionallysubstituted one to three times by halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy,C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy, cyano or nitro, especially halogenand Z is nitrogen or C—H.

Especially, Het is a group of the formula R₂, wherein X is sulfur, R⁷ ismethyl or ethyl, R⁸ is phenyl, phenyl substituted one to three times byhalogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy,cyano or nitro, and Z is nitrogen or C—H.

The invention relates also to the salts which the compounds of formula Iare able to form with amines, alkali metal and alkaline earth metalbases or quaternary ammonium bases. Among the alkali metal and alkalineearth metal hydroxides as salt formers, special mention should be madeof the hydroxides of lithium, sodium, potassium, magnesium and calcium,but especially the hydroxides of sodium and potassium. The compounds offormula I according to the invention also include hydrates which may beformed during the salt formation.

Examples of amines suitable for ammonium salt formation include ammoniaas well as primary, secondary and tertiary C₁-C₁₈alkylamines,C₁-C₄hydroxyalkylamines and C₂-C₄-alkoxyalkylamines, for examplemethylamine, ethylamine, n-propylamine, isopropylamine, the fourbutylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine,octyl-amine, nonylamine, decylamine, pentadecylamine, hexadecylamine,heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine,methylhexylamine, methyl-nonylamine, methylpentadecylamine,methyloctadecylamine, ethylbutylamine, ethylheptyl-amine,ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine,diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine,di-n-amylamine, diisoamylamine, dihexyl-amine, diheptylamine,dioctylamine, ethanolamine, n-propanolamine, isopropanolamine,N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine,allylamine, n-but-2-enyl-amine, n-pent-2-enylamine,2,3-dimethylbut-2-enylamine, dibut-2-enylamine, n-hex-2-enyl-amine,propylenediamine, trimethylamine, triethylamine, tri-n-propylamine,triisopropylamine, tri-n-butylamine, triisobutylamine,tri-sec-butylamine, tri-n-amylamine, methoxyethylamine andethoxyethylamine; heterocyclic amines, for example pyridine, quinoline,isoquinoline, morpholine, piperidine, pyrrolidine, indoline,quinuclidine and azepine; primary arylamines, for example anilines,methoxyanilines, ethoxyanilines, o-, m- and p-toluidines,phenylene-diamines, benzidines, naphthylamines and o-, m- andp-chloroanilines; but especially triethyl-amine, isopropylamine anddiisopropylamine.

Preferred quaternary ammonium bases suitable for salt formationcorrespond, for example, to the formula [N(R_(a)R_(b)R_(b)R_(d))]OHwherein R_(a), R_(b), R_(b) and R_(d) are each independently of theothers C₁-C₄alkyl. Further suitable tetraalkylammonium bases with otheranions can be obtained, for example, by anion exchange reactions.

Depending on the nature of the substituents G, R¹, R², R³, R⁴, R⁵, R⁶,R⁷ and R⁸, compounds of formula I may exist in different isomeric forms.When G is hydrogen, for example, compounds of formula I may exist indifferent tautomeric forms. This invention covers all such isomers andtautomers and mixtures thereof in all proportions. Also, whensubstituents contain double bonds, cis- and trans-isomers can exist.These isomers, too, are within the scope of the claimed compounds of theformula I.

A compound of formula I wherein G is C₁-C₈ alkyl, C₂-C₈ haloalkyl,phenylC₁-C₈alkyl (wherein the phenyl may optionally be substituted byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsufinyl, C₁-C₃ alkylsulfonyl, halogen, cyanoor by nitro), heteroarylC₁-C₈alkyl (wherein the heteroaryl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsufinyl, C₁-C₃ alkylsulfonyl,halogen, cyano or by nitro), C₃-C₈ alkenyl, C₃-C₈ haloalkenyl, C₃-C₈alkynyl, C(X^(a))—R^(a), C(X^(b))—X^(c)—R^(b), C(X^(d))—N(R^(c))—R^(d),—SO₂—R^(e), —P(X^(e))(R^(f))—R⁹ or CH₂—X^(f)—R^(h) where X^(a), X^(b),X^(c), X^(d), X^(e), X^(f), R^(a), R^(b), R^(c), R^(d), R^(e), R^(f),R^(g) and R^(h) are as defined above may be prepared by treating acompound of formula (A), which is a compound of formula I wherein G isH, with a reagent G-Z, wherein G-Z is alkylating agent such as an alkylhalide (the definition of alkyl halides includes simple C₁-C₈ alkylhalides such as methyl iodide and ethyl iodide, substituted alkylhalides such as chloromethyl alkyl ethers, Cl—CH₂—X^(f)—R^(h), whereinX^(f) is oxygen, and chloromethyl alkyl sulfides Cl—CH₂—X^(f)—R^(h),wherein X^(f) is sulfur), a C₁-C₈ alkyl sulfonate, or a di-C₁-C₈-alkylsulfate, or with a C₃-C₈ alkenyl halide, or with a C₃-C₈ alkynyl halide,or with an acylating agent such as a carboxylic acid, HO—C(X^(a))R^(a),wherein X^(a) is oxygen, an acid chloride, Cl—C(X^(a))R^(a), whereinX^(a) is oxygen, or acid anhydride, [R^(a)C(X^(a))]₂O, wherein X^(a) isoxygen, or an isocyanate, R^(c)N═C═O, or a carbamoyl chloride,Cl—C(X^(d))—N(R^(c))—R^(d) (wherein X^(d) is oxygen and with the provisothat neither R^(c) or R^(d) is hydrogen), or a thiocarbamoyl(X^(d))—N(R^(c))—R^(d) (wherein X^(d) is sulfur and with the provisothat neither R^(c) or R^(d) is hydrogen) or a chloroformate,Cl—C(X^(b))—X^(c)—R^(b), (wherein X^(b) and X^(c) are oxygen), or achlorothioformate Cl—C(X^(b))—X^(c)—R^(b) (wherein X^(b) is oxygen andX^(c) is sulfur), or a chlorodithioformate Cl—C(X^(b))—X^(c)—R^(b),(wherein X^(b) and X^(c) are sulfur), or an isothiocyanate, R^(c)N═C═S,or by sequential treatment with carbon disulfide and an alkylatingagent, or with a phosphorylating agent such as a phosphoryl chloride,Cl—P(X^(e))(R^(f))—R^(g) or with a sulfonylating agent such as asulfonyl chloride Cl—SO₂—R^(e), preferably in the presence of at leastone equivalent of base. Where substituents R¹ and R² are not equal tosubstituents R³ and R⁴, these reactions may produce, in addition to acompound of formula I, a second compound of formula IA. This inventioncovers both a compound of formula I and a compound of formula IA,together with mixtures of these compounds in any ratio.

The O-alkylation of cyclic 1,3-diones is known; suitable methods aredescribed, for example, in U.S. Pat. No. 4,436,666. Alternativeprocedures have been reported by M. Pizzorno and S. Albonico, Chem. Ind.(London), (1972), 425-426; H. Born et al., J. Chem. Soc., (1953),1779-1782; M. G. Constantino et al., Synth. Commun., (1992), 22 (19),2859-2864; Y. Tian et al., Synth. Commun., (1997), 27 (9), 1577-1582; S.Chandra Roy et al., Chem. Letters, (2006), 35 (1), 16-17; P. Zubaidha etal., Tetrahedron Lett., (2004), 45, 7187-7188.

The O-acylation of cyclic 1,3-diones may be effected by proceduressimilar to those described, for example, by R. Haines, U.S. Pat. No.4,175,135, and by T. Wheeler, U.S. Pat. No. 4,422,870, U.S. Pat. No.4,659,372 and U.S. Pat. No. 4,436,666. Typically diones of formula (A)may be treated with the acylating agent in the presence of at least oneequivalent of a suitable base, optionally in the presence of a suitablesolvent. The base may be inorganic, such as an alkali metal carbonate orhydroxide, or a metal hydride, or an organic base such as a tertiaryamine or metal alkoxide. Examples of suitable inorganic bases includesodium carbonate, sodium or potassium hydroxide, sodium hydride, andsuitable organic bases include trialkylamines, such as trimethylamineand triethylamine, pyridines or other amine bases such as1,4-diazobicyclo[2.2.2]octane and 1,8-diazabicyclo[5.4.0]undec-7-ene.Preferred bases include triethylamine and pyridine. Suitable solventsfor this reaction are selected to be compatible with the reagents andinclude ethers such as tetrahydrofuran and 1,2-dimethoxyethane andhalogenated solvents such as dichloromethane and chloroform. Certainbases, such as pyridine and triethylamine, may be employed successfullyas both base and solvent. For cases where the acylating agent is acarboxylic acid, acylation is preferably effected in the presence of acoupling agent such as 2-chloro-1-methylpyridinium iodide,N,N′-dicyclohexylcarbodiimide,1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and N,N′ carbodiimidazole,and a base such as triethylamine or pyridine in a suitable solvent suchas tetrahydrofuran, dichloromethane or acetonitrile. Suitable proceduresare described, for example, by W. Zhang and G. Pugh, Tetrahedron Lett.,(1999), 40 (43), 7595-7598 and T. Isobe and T. Ishikawa, J. Org. Chem.,(1999), 64 (19), 6984.

Phosphorylation of cyclic 1,3-diones may be effected using a phosphorylhalide or thiophosphoryl halide and a base by procedures analogous tothose described by L. Hodakowski, U.S. Pat. No. 4,409,153.

Sulfonylation of a compound of formula (A) may be achieved using analkyl or aryl sulfonyl halide, preferably in the presence of at leastone equivalent of base, for example by the procedure of C. Kowalski andK. Fields, J. Org. Chem., (1981), 46, 197.

Compounds of formula (A), wherein Y is S(O)_(m) and m is 1 or 2 may beprepared from compounds of formula (A) wherein Y is S by oxidation,according to the procedure of E. Fehnel and A. Paul, J. Am. Chem. Soc.,(1955), 77, 4241.

Compounds of formula (A), wherein Y is O, S or C═O may be prepared viathe cyclisation of compounds of formula (B), preferably in the presenceof an acid or base, and optionally in the presence of a suitablesolvent, by analogous methods to those described by T. Teresawa and T.Okada, J. Org. Chem., (1977), 42 (7), 1163-1167 and by T. Wheeler, U.S.Pat. No. 4,209,532. The compounds of the formula (B) have beenparticularly designed as intermediates in the synthesis of the compoundsof the formula I. Compounds of formula (B) wherein R is hydrogen may becyclised under acidic conditions, preferably in the presence of a strongacid such as sulfuric acid, polyphosphoric acid or Eaton's reagent,optionally in the presence of a suitable solvent such as acetic acid,toluene or dichloromethane.

Compounds of formula (B) wherein R is alkyl (preferably methyl or ethyl)may be cyclised under acidic or, preferably basic conditions, preferablyin the presence of at least one equivalent of a strong base such aspotassium tert-butoxide, lithium diisopropylamide or sodium hydride andin a solvent such as tetrahydrofuran, toluene, dimethylsulfoxide orN,N-dimethylformamide.

The compounds of the formula B are novel and have been designedparticularly for the synthesis of the inventive compounds of the formulaI. Compounds of formula (B), wherein R is H may be prepared bysaponification of compounds of formula (C) wherein R¹ is alkyl(preferably methyl or ethyl) under standard conditions, followed byacidification of the reaction mixture to effect decarboxylation, bysimilar processes to those described, for example, by T. Wheeler, U.S.Pat. No. 4,209,532:

Compounds of formula (C), wherein R is H may be esterified to compoundsof formula (C), wherein R is alkyl, under standard conditions.

Compounds of formula (C) wherein R is alkyl may be prepared by treatingcompounds of formula (D) with suitable carboxylic acid chlorides offormula (E) wherein R is alkyl under basic conditions. Suitable basesinclude potassium tert-butoxide, sodium bis(trimethylsilyl)amide andlithium diisopropylamide and the reaction is preferably conducted in asuitable solvent (such as tetrahydrofuran or toluene) at a temperatureof between −80° C. and 30° C.:

Alternatively, compounds of formula (C), wherein R is H, may be preparedby treating compounds of formula (D) with a suitable base (such aspotassium tert-butoxide, sodium bis(trimethylsilyl)amide and lithiumdiisopropylamide) in a suitable solvent (such as tetrahydrofuran ortoluene) at a suitable temperature (between −80° C. and 30° C.) andreacting the resulting anion with a suitable anhydride of formula (F).

Compounds of formula (E) and formula (F) are known (see, for example T.Terasawa and T. Okada, J. Org. Chem., 1977, 42 (7), 1163) or may be madeby similar methods from commercially available starting materials.Compounds of formula (D) are known, or may be made by known methods fromknown compounds (see, for example, E. Bellur and P. Langer, Synthesis(2006), 3, 480-488; E. Bellur and P. Langer, Eur. J. Org. Chem., (2005),10, 2074-2090; G. Bartolo et al., J. Org. Chem., (1999), 64 (21),7693-7699; R. Kranich et al., J. Med. Chem., (2007), 50 (6), 1101-1115;I. Freifeld et al., J. Org. Chem., (2006) 71 (13), 4965-4968; S. Hermannet al., WO2006/087120; R. Fischer et al. WO96/16061; H. Staab and G.Schwalbach, Justus Liebigs Annalen der Chemie, (1968), 715, 128-34; J-LBrayer et al., EP402246; P. Chemla et al., WO99/32464; A. Dornow and G.Petsch, Chem. Berichte, (1953), 86, 1404-1407; E. Y-H Chao et al.,WO2001/000603; D. B. Lowe et al., WO2003/011842; R. Fischer et al.,WO2001/096333; J. Ackermann et al., WO2005/049572; B. Li et al., Bioorg.Med. Chem. Lett., (2002), 12, 2141-2144, G. P. Rizzi, J. Org. Chem.,(1968), 33 (4) 13333-13337; M. Okitsu and K. Yoshid, JP63230670; F.Bohlmann et al., Chem. Ber., (1955), 88, 1831-1838; R. Fischer et al.,WO2003/035463; R. Fischer er al., WO2005/005428; D O'Mant, GB1226981).

Alternatively, a compound of formula (B), wherein Y is O or S, may beprepared from a known compound of formula (G), wherein Y is O or S, byalkylation with a compound of formula (H), wherein L is a leaving groupsuch as a halogen or an alkyl-sulfonate or an aryl-sulfonate andpreferably one or both of R³ and R⁴ is hydrogen. Preferably the reactionis conducted in the presence of a suitable base and optionally in thepresence of a suitable solvent.

The base may be an inorganic base such as an alkali metal hydroxide,carbonate, or a metal hydride, or an organic base such as a tertiaryamine or an alkali metal alkoxide. Examples of suitable inorganic basesinclude sodium carbonate, potassium carbonate, lithium hydroxide, sodiumhydroxide, potassium hydroxide or sodium hydride, and suitable organicbases include amines such as trimethylamine or triethylamine,piperidine, pyridine and 4-diazobicyclo[2.2.2]octane. Where employed,solvents for this reaction are selected to be compatible with thereagents and include, for example, ethers such as diethyl ether,1,2-dimethoxyethane and tetrahydrofuran, aliphatic ketones such asmethyl isobutylketone and acetone, aliphatic alcohols such as methanol,ethanol and isopropanol, amides such as N,N-dimethylformamide,N,N-dimethylacetamide, and N-methylpyrrolidone, aromatic hydrocarbonssuch as toluene and xylene, acetonitrile and halogenated solvents suchas dichloromethane and chloroform. Certain bases, such as pyridine andtriethylamine, may be employed successfully as both base and solvent.

Compounds of formula (H) are known compounds or may be made my knownmethods from known compounds (see, for example, N. Kaila et al., J. Med.Chem. (2007), 50 (1), 40-64).

Alternatively, a compound of formula (B) wherein Y is O or S andpreferably one or both of R¹ and R² is hydrogen may be prepared from acompound of formula (J) by reaction with a known compound of formula (K)under conditions similar to those used to prepare a compound of formula(B) from a compound of formula (G).

Compounds of formula (J) are known compounds, or may be made from knowncompounds by known methods. (see, for example, N. Kaila et al., J. Med.Chem. (2007), 50 (1), 40-64; E. Reimann, EP647640; V. Dalla and J.Catteau, Tetrahedron, (1999), 55, 6497-6510)).

In a further approach to compounds of formula (B), a compound of formula(B) wherein Y is O or S and R² is hydrogen may be prepared from acompound of formula (L) and a known diazoester of formula (M) by aphotochemical or metal catalysed O—H and S—H insertion, by proceduresdescribed by, for example by D. Miller and C. Moody, Tetrahedron,(1995), 51, 10811-10843.

Preferably the metal catalyst is a transition metal catalyst, morepreferably a rhodium (II) catalyst such as rhodium (II) acetate, or acopper catalyst such as copper (II) trifluoromethanesulfonate or copper(II) acetylacetonate, and the reaction is preferably carried out in asolvent such as dichloromethane or toluene.

Using similar methods, a compound of formula (B) wherein Y is O or S andR⁴ is hydrogen may also be prepared by reacting a diazoketone of formula(N) with a known compound of formula (O), preferably in the presence ofa suitable catalyst and in a suitable solvent under conditions outlinedabove.

Compounds of formula (N) are known compounds or may be prepared by knownmethods (for example by reaction of a known acid chloride of formula (P)with a diazoalkane under conditions described in the literature (see,for example, A. Boularot et al., J. Med. Chem., (2007, 50 (1), 10-20; M.Salim and A. Capretta, Tetrahedron (2000); 56, 8063-8069; K Yong et al.,J. Org. Chem., (1998); 63 (26), 9828-9833; A. Padwa et al., J. Org.Chem., (1989), 54 (2), 299-308)

In a further approach to compounds of formula (A), a compound of formula(O), which is a compound of formula (A) wherein Het is (R₂) when R⁷ isCH₂R″ and R″ is hydrogen, alkyl or halogenoalkyl (preferably hydrogen,methyl or trifluoromethyl), may be prepared by rearrangement of acompound of formula (R), optionally in the presence of a suitablesolvent and optionally under microwave irradiation.

Preferably, the rearrangement is effected by heating a compound offormula (G) at temperatures of between 120-300° C., optionally in asuitable solvent such as 1,2-dimethoxy-ethane, diethylene glycol methylether, xylene, mesitylene or Dowtherm®, and optionally under microwaveirradiation.

Similarly, a compound of formula (S), which is a compound of formula (A)wherein Het is (R₃) when R⁷ is CH₂R″ and R″ is hydrogen, alkyl orhalogenoalkyl (preferably hydrogen, methyl or trifluoromethyl), may beprepared from a compound of formula (T) using similar methods.

A compound of formula (R) may be prepared from a compound of formula (U)by alkylation with a compound of formula (V), wherein L is a suitableleaving group such as a halogen or an alkyl- or aryl-sulfonate,optionally in the presence of a suitable base and optionally in asuitable solvent as described above for the alkylation of compounds offormula (A)

Similarly, a compound of formula (T) may be prepared from a compound offormula (U) by alkylation with a compound of formula (W), wherein L is asuitable leaving group such as a halogen or an alkyl- or aryl-sulfonate,under similar conditions.

In an alternative approach, a compound of formula (R) may be preparedfrom a compound of formula (U) by condensation with an alcohol offormula (X), optionally in the presence of a suitable acid catalyst suchas p-toluenesulfonic acid, or a Lewis acid catalyst, for example,ytterbium (III) trifluoromethanesulfonate, lanthanum (III)trifluoromethanesulfonate, sodium tetrachloroaurate (III) dihydrate,titanium (IV) chloride, indium (III) chloride or aluminium chloride, andoptionally in a suitable solvent. Suitable solvents are selected to becompatible with the reagents used, and include, for example, toluene,ethanol or acetonitrile. Similar approaches have been described by, forexample, M. Curini; F. Epifano, S. Genovese, Tetrahedron Lett., (2006),47, 4697-700; A. Arcadi, G. Bianchi, S. Di Giuseppe, and by F.Marinelli, Green Chemistry, (2003), 5, 64-7.

Alternatively, the condensation may be effected in the presence ofsuitable coupling agents such as 2-chloro-1-methylpyridinium iodide,N,N′-dicyclohexylcarbodiimide,1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and N,N-carbodiimidazoleand a suitable base such a triethylamine or pyridine in a suitablesolvent such as tetrahydrofuran, acetonitrile or dichloromethane, or inthe presence of a triarylphosphine (such as triphenylphosphine) and adialkyl azidodicarboxylate (preferably diethyl azidodicarboxylate ordiisopropyl azidodicarboxylate) and in a suitable solvent such asdiethyl ether, tetrahydrofuran or 1,4-dioxane as described, for example,by O. Mitsunobu, Synthesis (1981), 1, 1-28.

Using similar processes, a compound of formula (T) may be prepared byreaction of a compound of formula (U) with a compound of formula (Y).

Additional compounds of formula (R) wherein R⁸ is an aromatic orheteroaromatic moiety, or is an alkyl, alkenyl or alkynyl group, may beprepared by the reaction of a compound of formula (Z), wherein Q is anatom or group suitable for undergoing cross-coupling reactions (forexample Q is chlorine, bromine or iodine, or a haloalkylsulfonate suchas trifluoromethanesulfonate), and R″ is as defined for a compound offormula (Q), with a suitable coupling partner under conditions describedin the literature for Suzuki-Miyaura, Sonogashira, Stifle and relatedcross-coupling reactions.

For example, a compound of formula (Z) may be treated with an aryl-,heteroaryl-, alkyl-, alkenyl- or alkynylboronic acid, R⁸—B(OH)₂,boronate ester, R⁸—B(OR′″)₂, (preferably an ester wherein the fragment—B(OR′″)₂ represents a cyclic boronate ester derived from a 1,2- or a1,3-alkanediol, such as pinacol, 2,2-dimethyl-1,3-propanediol and2-methyl-2,4-pentanediol), or a metal (especially potassium) aryl-,heteroaryl, alkyl-, alkenyl- and alkynyltrifluoroborate salt,M⁺[R⁸—BF₃]⁺ in the presence of a suitable palladium catalyst, a suitableligand and a suitable base in the presence of a suitable solvent, underSuzuki-Miyaura conditions (see, for example I. Kondolff, H. Doucet andM, Santelli, Tetrahedron, (2004), 60, 3813-3818; F. Bellina, A. Carpitaand R. Rossi, Synthesis (2004), 15, 2419-2440; G. Molander and C—S Yun,Tetrahedron, (2002), 58, 1465-1470; G. Zou, Y. K. Reddy and J. Falck,Tetrahedron Lett., (2001), 42, 4213-7215; A. Suzuki, Journal ofOrganometallic Chemistry, (2002), 653, 83; H. Stefani, R. Cella and A.Vieira, Tetrahedron, (2007), 62, 3623-3658; G. Molander, C—S Yun, M.Ribagorda and B. Biolatto, J. Org. Chem., (2003), 68, 5534-5539; S.Darses, G. Michaud and J-P, Genêt, Eur. J. Org. Chem., (1999),1877-1883; K. Billingsley and S. Buchwald, J. Am. Chem. Soc., (2007),129, 3358-3366).

Similarly, a compound of formula (T) may be prepared from a compound offormula (AA), wherein Q is as defined previously, and R″ is as definedfor a compound of formula (Z), by analogous methods using appropriatestarting materials.

A compound of formula (Z) may be prepared from a compound of formula(U), by reaction with a compound of formula (BB) wherein L is a suitableleaving group such as a halogen or an alkyl- or aryl-sulfonate, byprocesses analogous to those described above for the preparation of acompound of formula (R) from a compound of formula (U). Alternatively, acompound of formula (Z) may be prepared by reaction of a compound offormula (L) with a compound of formula (CC) by processes analogous tothose described above for the preparation of a compound of formula (R)from a compound of formula (L).

By analogous processes to those described above, a compound of formula(AA) may be prepared from a compound of formula (U) by alkylation with acompound of formula (DD), wherein L is a suitable leaving group such asa halogen or an alkyl- or aryl-sulfonate, or by alkylation with acompound of formula (EE).

In an alternative approach, a compound of formula (U) may be treatedwith a halogenating agent such as phosphorus oxychloride, phosphoruspentachloride, phosphorus pentabromide, phosphorus oxybromide, oxalylchloride or oxalyl bromide, optionally in a suitable solvent such astoluene, chloroform, dichloromethane with optionally the presence ofdimethylformamide, and the resulting vinyl halide of formula (FF),wherein Hal is chlorine or bromine may be converted by reaction with analcohol of formula (X), or of formula (Y), or of formula (CC) or offormula (EE) optionally in the presence of a suitable base such assodium hydride, sodium tert-butoxide, potassium tert-butoxide and asuitable solvent such as tetrahydrofuran, 1,4-dioxane, diethylene glycoldimethyl ether to give a compound of formula (R), formula (T), formula(Z) and formula (AA) respectively:

Compounds of formula (V), formula (W), formula (X), formula (Y), formula(BB), formula (CC), formula (DD) and formula (EE) are known or may beprepared by known methods from known compounds (see, for example T.Denton, X. Zhang, J. Cashman, J. Med. Chem., (2005), 48, 224-239; J.Reinhard, W. Hull, C.-W. von der Lieth, U. Eichhorn, H.-C. Kliem, J.Med. Chem., (2001), 44, 4050-4061; H. Kraus and H. Fiege, DE19547076; M.Boys, L. Schretzman, N. Chandrakumar, M. Tollefson, S. Mohler, V. Downs,T. Penning, M. Russell, J. Wendt, B. Chen, H. Stenmark, H. Wu, D.Spangler, M. Clare, B. Desai, I. Khanna, M. Nguyen, T. Duffin, V.Engleman, M. Finn, S. Freeman, M. Hanneke, J. Keene, J. Klover, G. A.Nickols, M. Nickols, C. Steininger, M. Westlin, W. Westlin, Y. Yu, Y.Wang, C. Dalton, S. A. Norring, Bioorg. Med. Chem. Lett., (2006), 16,839-844; A. Silberg, A. Benko, G. Csavassy, Chem. Ber., (1964), 97,1684-1687; K. Brown and R. Newbury, Tetrahedron Lett., (1969), 2797; A.Jansen and M. Szelke, J. Chem. Soc., (1961), 405; R. Diaz-Cortes, A.Silva and L. Maldonado, Tetrahedron Lett., (1997), 38(13), 2007-2210; M.Friedrich, A. Waechtler and A. De Meijure, Synlett., (2002), 4, 619-621;F. Kerdesky and L. Seif, Synth. Commun., (1995), 25 (17), 2639-2645; Z.Zhao, G. Scarlato and R. Armstrong., Tetrahedron Lett., (1991), 32 (13),1609-1612; K-T. Kang and S. Jong, Synth. Commun. (1995), 25 (17),2647-2653; M. Altamura and E. Perrotta, J. Org. Chem., (1993), 58 (1),272-274).

Compounds of formula (U), wherein Y is O, are known compounds or may beprepared by routes analogous to those described in the literature (see,for example, M. Morgan and E. Heyningen, J. Am. Chem. Soc., (1957), 79,422-4; I. K. Korobitsyna and K. Pivnitskii, Zhurnal Obshchei Khimii,(1960), 30, 4016-4023; T. Terasawa, and T. Okada, J. Org. Chem., (1977),42 (7), 1163; R. Anderson et al. US 1988/156269; R. Altenbach, K.Agrios, I. Drizin and W. Carroll, Synth. Commun., (2004), 34 (4)557-565; R. Beaudegnies et al., WO2005/123667; W. Li, G. Wayne, J.Lallaman, S. Chang, and S. Wittenberger, J. Org. Chem. (2006), 71,1725-1727; R. Altenbach, M. Brune, S. Buckner, M. Coghlan, A. Daza, A.Fabiyi, M. Gopalakrishnan, R. Henry, A. Khilevich, M. Kort, I. Milicic,V. E. Scott, J. Smith, K. Whiteaker, and W. Carroll, J. Med. Chem.,(2006), 49(23), 6869-6887. Compounds of formula (U), wherein Y is S, areknown compounds or may be prepared by routes analogous to thosedescribed in the literature (see, for example, E. Fehnel and A. Paul, J.Am. Chem. Soc., (1955), 77, 4241; E. Er and P. Margaretha, HelveticaChimica Acta (1992), 75(7), 2265-69; H. Gayer et al., DE 3318648 A1).Compounds of formula (U), wherein Y is C═O, are known compounds or maybe prepared by routes analogous to those described in the literature(see, for example, R. Gotz et al. WO2000/075095).

In a further approach, a compound of formula (A) wherein Y is O, S orC═O, may be prepared by reaction of a compound of formula (U) with aheteroaryl lead tricarboxylate under conditions described in theliterature (for example see, J. Pinhey and B. Rowe, Aust. J. Chem.,(1979), 32, 1561-6; J. Morgan and J. Pinhey, J. Chem. Soc. Perkin Trans.1, (1990), 3, 715-20; J. Pinhey and E. Roche, J. Chem. Soc. PerkinTrans. 1, (1988), 2415-21). Preferably the heteroaryl leadtricarboxylate is a heteroaryl triacetate of formula (GG) and thereaction is conducted in the presence of a suitable ligand (for exampleN,N-dimethylaminopyridine, pyridine, imidazole, bipyridine, and1,10-phenanthroline, preferably one to ten equivalents ofN,N-dimethylaminopyridine with respect to compound (U)) and in asuitable solvent (for example chloroform, dichloromethane and toluene,preferably chloroform and optionally in the presence of a co-solventsuch as toluene) at 25° C. to 100° C. (preferably 60-90° C.).

A compound of formula (GG) may be prepared from a compound of formula(HH) by treatment with lead tetraacetate in a suitable solvent (forexample chloroform) at 25° C. to 100° C. (preferably 25-50° C.),optionally in the presence of a catalyst such as mercury diacetate,according to procedures described in the literature (for example see, K.Shimi, G. Boyer, J-P. Finet and J-P. Galy, Letters in Organic Chemistry,(2005), 2, 407-409; J. Morgan and J. Pinhey, J. Chem. Soc. Perkin Trans.1; (1990), 3, 715-20).

Preferred coupling partners include heteroarylboronic acids, (HH₁) to(HH₈), wherein R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², X, W¹, W², W³, W⁴ and Z are asdefined above.

Heteroarylboronic acids of formula (HH) are known compounds, or may beprepared from known compounds by known methods (see for example A.Voisin et al., Tetrahedron (2005); 1417-1421; A. Thompson et al.,Tetrahedron (2005), 61, 5131-5135; K. Billingsley and S. Buchwald, J.Am. Chem. Soc., (2007), 129, 3358-3366; N. Kudo, M. Pauro and G. Fu,Angew. Chem. Int. Ed., (2006), 45, 1282-1284; A. Ivachtchenko et al., J.Heterocyclic Chem., (2004), 41(6), 931-939; H. Matondo et al., Synth.Commun., (2003), 33 (5) 795-800; A. Bouillon et al., Tetrahedron,(2003), 59, 10043-10049; W. Li et al., J. Org. Chem., (2002), 67,5394-5397; C. Enguehard et al., J. Org. Chem. (2000), 65, 6572-6575; H—NNguyen, X. Huang and S. Buchwald, J. Am. Chem. Soc., (2003), 125,11818-11819, and references therein).

In a further approach, a compound of formula (A) may be prepared fromcompounds of formula (JJ) by reaction with a heteroaryl boronic acid offormula (HH), in the presence of a suitable palladium catalyst and abase, and preferably in a suitable solvent.

Suitable palladium catalysts are generally palladium(II) or palladium(0)complexes, for example palladium(II) dihalides, palladium(II) acetate,palladium(II) sulfate, bis(triphenylphosphine)palladium(II) dichloride,bis(tricyclopentylphosphine)palladium(II) dichloride,bis(tricyclohexylphosphine)palladium(II) dichloride,bis(dibenzylideneacetone)palladium(0) ortetrakis(triphenylphosphine)palladium(0). The palladium catalyst canalso be prepared “in situ” from palladium(II) or palladium(0) compoundsby complexing with the desired ligands, by, for example, combining thepalladium(II) salt to be complexed, for example palladium(II) dichloride(PdCl₂) or palladium(II) acetate (Pd(OAc)₂), together with the desiredligand, for example triphenyl-phosphine (PPh₃), tricyclopentylphosphineor tricyclohexylphosphine and the selected solvent, with a compound offormula (JJ), a heteroaromatic boronic acid of formula (HH) and a base.Also suitable are bidendate ligands, for example1,1′-bis(diphenyl-phosphino)ferrocene or1,2-bis(diphenylphosphino)ethane. By heating the reaction medium, thepalladium(II) complex or palladium(0) complex desired for the C—Ccoupling reaction is thus formed “in situ”, and then initiates the C—Ccoupling reaction. The palladium catalysts are used in an amount of from0.001 to 50 mol %, preferably in an amount of from 0.1 to 15 mol %,based on the compound of formula (JJ). More preferably the palladiumsource is palladium acetate, the base is lithium hydroxide and thesolvent is a mixture of 1,2-dimethoxyethane and water in a ratio of 4:1to 1:4. The reaction may also be carried out in the presence of otheradditives, such as tetralkylammonium salts, for example,tetrabutylammonium bromide:

A compound of formula (JJ) may be prepared from a compound of formula(U) by treatment with (diacetoxy)iodobenzene according to the proceduresof K. Schank and C. Lick, Synthesis, (1983), 392, or of Z Yang et al.,Org. Lett., (2002), 4 (19), 3333.

In a further approach a compound of formula (A) may be prepared via therearrangement of a compound of formula (KK), in the presence of areagent which promotes rearrangement, such as a metal alkoxide(preferably in an amount equal to or greater than 100% with respect tocompound of formula (KK)) or cyanide anion, for example 0.001-25%potassium cyanide, 0.001-25% sodium cyanide, or 0.001-25% acetonecyanohydrin with respect to a compound of formula (KK). This reaction isalso optionally performed in a suitable solvent (for exampleacetonitrile) at a suitable temperature (typically 25-100° C.) with asuitable base (such as triethylamine).

A compound of formula (KK) may be prepared from a compound of formula(LL) by treatment with a catalyst such as palladium(II) dichloride orsilver carbonate (preferably 0.001-50% silver carbonate with respect tocompound of formula (LL)), in the presence of a suitable solvent (forexample acetonitrile) at a suitable temperature (typically 25° C. to150° C., preferably 120° C. under microwave heating). Similarlactonisations are known in the literature (see for example P. Huang andW. Zhou, Tetrahedron Asymmetry (1991), 2(9), 875-878.)

A compound of formula (LL) may be prepared by the saponification of acompound of formula (MM) where R″″ is alkyl (preferably methyl or ethyl)under known conditions, and a compound of formula (MM) may be preparedfrom a compound of formula (NN) by Sonogashira coupling with a suitableheteroaromatic halide, (such as a bromide or iodide), Het-hal, in thepresence of a palladium catalyst (for example bis(triphenylphosphine)palladium(II) dichloride in an amount typically 0.001-25% of compound offormula (NN)), copper source (for example copper(I) iodide in an amounttypically 0.001-50% of compound of formula (NN)), base (such asdiethylamine or triethylamine), and optionally in a suitable solvent.Similar couplings are known in the literature (see for example see, Z.Gan and R. Roy, Canadian Journal of Chemistry (2002), 80(8), 908-916).

Compounds of formula (NN) are known compounds or may be prepared byroutes analogous to those described in the literature (see, for example,I. Drizin et al, WO2001/066544; M. Yamamoto, Journal of ChemicalResearch, Synopses (1991), (7), 165; P. Machin, U.S. Pat. No. 4,774,253;M. Morgan and E. Heyningen, J. Am. Chem. Soc., (1957), 79, 422-424).

In a further approach, a compound of formula (A) may be prepared from acompound of formula I or IA (wherein G is C₁₋₄ alkyl) by hydrolysis,preferably in the presence of an acid catalyst such as hydrochloric acidand optionally in the presence of a suitable solvent such astetrahydrofuran. A compound of formula I (wherein G is preferably C₁₋₄alkyl) may be prepared by reacting a compound of formula (OO) (wherein Gis preferably C₁₋₄ alkyl, and Hal is a halogen, preferably bromine oriodine), with a heteroaryl boronic acid, Het-B(OH)₂, of formula (HH) inthe presence of a suitable palladium catalyst (for example 0.001-50%palladium(II) acetate with respect to compound (OO) and a base (forexample 1 to 10 equivalents potassium phosphate with respect to compound(OO) and preferably in the presence of a suitable ligand (for example0.001-50% (2-dicyclohexylphosphino)-2′,6′-dimethoxybiphenyl with respectto compound (OO), and in a suitable solvent (for example toluene),preferably between 25° C. and 200° C. Similar couplings are known in theliterature (see for example, Y. Song, B. Kim and J.-N. Heo, TetrahedronLetters (2005), 46(36), 5987-5990).

A compound of formula (O) may be prepared by halogenating a compound offormula (U), followed by alkylation of the resulting halide of formula(PP) with a C₁₋₄ alkyl halide or tri-C₁₋₄-alkylorthoformate under knownconditions, for example by the procedures of R. Shepherd and A. White(J. Chem. Soc. Perkin Trans. 1 (1987), 2153-2155) and Y.-L. Lin et al.(Bioorg. Med. Chem. (2002), 10, 685-690). Alternatively, a compound offormula (O) may be prepared by alkylating a compound of formula (U) witha C₁₋₄ alkyl halide or a tri-C₁₋₄-alkylorthoformate, and halogenatingthe resulting enone of formula (QQ) under known conditions (see forexample Y. Song, B. Kim and J.-N. Heo, Tetrahedron Letters (2005),46(36), 5987-5990).

In a further approach, a compound of formula (A) may be prepared byreacting a compound of formula (U) with a suitable heteroaryl halide(such as an iodide or bromide), Het-hal, in the presence of a suitablepalladium catalyst (for example 0.001-50% palladium(II) acetate withrespect to compound (U)) and a base (for example 1 to 10 equivalentspotassium phosphate with respect to compound (U)) and preferably in thepresence of a suitable ligand (for example 0.001-50%(2-dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl with respect tocompound (U)), and in a suitable solvent (for example dioxane),preferably between 25° C. and 200° C. Similar couplings are known in theliterature (see for example, J. Fox, X. Huang, A. Chieffi, and S.Buchwald, J. Am. Chem. Soc. (2000), 122, 1360-1370; B. Hong et al. WO2005/000233). Alternatively, a compound of formula (A) may be preparedby reacting a compound of formula (U) with a suitable heteroaryl halide(such as an iodide or bromide), Het-hal, in the presence of a suitablecopper catalyst (for example 0.001-50% copper(I) iodide with respect tocompound (U)) and a base (for example 1 to 10 equivalents potassiumcarbonate with respect to compound (U)) and preferably in the presenceof a suitable ligand (for example 0.001-50% L-proline with respect tocompound (U)), and in a suitable solvent (for exampledimethylsulfoxide), preferably between 25° C. and 200° C. Similarcouplings are known in the literature for aryl halides (see for example,Y. Jiang, N. Wu, H. Wu, and M. He, Synlett, (2005), 18, 2731-2734).

Those skilled in the art will appreciate that compounds of formula I maycontain a heteroaromatic moiety bearing one or more substituents capableof being transformed into alternative substituents under knownconditions, and that these compounds may themselves serve asintermediates in the preparation of additional compounds of formula I.For example, a heterocycle of formula (RR) wherein Q₁ is alkenyl oralkynyl, may be reduced to a compound of formula (Q) wherein R⁸ is alkylunder known conditions.

Furthermore, a compound of formula (RR) wherein Q₁ is an atom or groupsuitable for cross-coupling chemistry such as a halogen or ahaloalkylsulfonate may undergo Suzuki-Miyaura, Stille, Sonogashira andrelated reactions under known conditions to give additional compounds offormula Q.

Those skilled in the art will appreciate that transformations of thistype are not restricted to compounds of formula (RR), but may in generalbe applied to any compound of formula I where Het is a heterocyclesubstituted by an atom or group Q₁ suitable for further derivatisation.

In a further approach to compounds of formula (A), wherein Het is agroup of formula (R₂), X is S, and Y is N, a compound of formula (SS)wherein Lisa suitable leaving group such as a halogen or an alkyl- orhaloalkylsulfonate, may be treated with a compound of formula (TT),optionally in the presence of a suitable base (such as triethylamine orpyridine), and optionally in a suitable solvent (such as water, toluene,acetone, ethanol or isopropanol) according to known procedures, (see,for example, E. Knott, J. Chem. Soc., (1945), 455; H. Brederick, R.Gompper, Chem. Ber. (1960), 93, 723; B. Friedman, M. Sparks and R.Adams, J. Am. Chem. Soc., (1937), 59, 2262).

Alternatively, a compound of formula (SS) may be treated with thiourea,by known procedures (see, for example, V. Pshenichniya, O. Gulyakevichand V. Kripach, Chemistry of Heterocyclic Compounds, (1990), 10,1409-1412), and the resulting product of formula (UU) may be convertedinto additional compounds of formula (A) by conversion to a halide offormula (VV), wherein Hal is chlorine, bromine or iodine, underSandmeyer conditions, and a compound of formula (W) may be converted tocompounds of formula (A) by cross-coupling under known conditions forthe Suzuki-Miyaura, Sonogashira, Stille and related reactions, asdescribed previously.

A compound of formula (SS) may be prepared from a compound of formula(U) under known conditions (see, for example, V. Pshenichniya, O.Gulyakevich and V. Kripach, Chemistry of Heterocyclic Compounds, (1990),10, 1409-1412; V. Pshenichniya, O. Gulyakevich and V. Kripach, RussianJournal of Organic Chemistry, (1989), 25 (9), 1882-1888).

The compounds of the formulae (B), (R) and (T) are novel and have beenspecifically designed for the synthesis of the compounds of the formulaI.

The compounds of formula I according to the invention can be used asherbicides in unmodified form, as obtained in the synthesis, but theyare generally formulated into herbicidal compositions in a variety ofways using formulation adjuvants, such as carriers, solvents andsurface-active substances. The formulations can be in various physicalforms, for example in the form of dusting powders, gels, wettablepowders, water-dispersible granules, water-dispersible tablets,effervescent compressed tablets, emulsifiable concentrates,microemulsifiable concentrates, oil-in-water emulsions, oil flowables,aqueous dispersions, oily dispersions, suspoemulsions, capsulesuspensions, emulsifiable granules, soluble liquids, water-solubleconcentrates (with water or a water-miscible organic solvent ascarrier), impregnated polymer films or in other forms known, forexample, from the Manual on Development and Use of FAO Specificationsfor Plant Protection Products, 5th Edition, 1999. Such formulations caneither be used directly or are diluted prior to use. Dilutedformulations can be prepared, for example, with water, liquidfertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared, for example, by mixing the activeingredient with formulation adjuvants in order to obtain compositions inthe form of finely divided solids, granules, solutions, dispersions oremulsions. The active ingredients can also be formulated with otheradjuvants, for example finely divided solids, mineral oils, vegetableoils, modified vegetable oils, organic solvents, water, surface-activesubstances or combinations thereof. The active ingredients can also becontained in very fine microcapsules consisting of a polymer.Microcapsules contain the active ingredients in a porous carrier. Thisenables the active ingredients to be released into their surroundings incontrolled amounts (e.g. slow release). Microcapsules usually have adiameter of from 0.1 to 500 microns. They contain active ingredients inan amount of about from 25 to 95% by weight of the capsule weight. Theactive ingredients can be present in the form of a monolithic solid, inthe form of fine particles in solid or liquid dispersion or in the formof a suitable solution. The encapsulating membranes comprise, forexample, natural and synthetic gums, cellulose, styrene-butadienecopolymers, polyacrylonitrile, polyacrylate, polyester, polyamides,polyureas, polyurethane or chemically modified polymers and starchxanthates or other polymers that are known to the person skilled in theart in this connection. Alternatively it is possible for very finemicrocapsules to be formed wherein the active ingredient is present inthe form of finely divided particles in a solid matrix of a basesubstance, but in that case the microcapsule is not encapsulated.

The formulation adjuvants suitable for the preparation of thecompositions according to the invention are known per se. As liquidcarriers there may be used: water, toluene, xylene, petroleum ether,vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acidanhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone,butylenes carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkylesters of acetic acid, diacetone alcohol, 1,2-dichloropropane,diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycolabietate, diethylene glycol butyl ether, diethylene glycol ethyl ether,diethylene glycol methyl ether, N,N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methylether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone,ethyl acetate, 2-ethyl hexanol, ethylene carbonate,1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyllactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycolmethyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glyceroldiacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamylacetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene,isopropyl myristate, lactic acid, laurylamine, mesityl oxide,methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyllaurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene,n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleicacid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400),propionic acid, propyl lactate, propylene carbonate, propylene glycol,propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate,triethylene glycol, xylenesulfonic acid, paraffin, mineral oil,trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butylacetate, propylene glycol methyl ether, diethylene glycol methyl ether,methanol, ethanol, isopropanol, and higher molecular weight alcohols,such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol,ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone andthe like. Water is generally the carrier of choice for the dilution ofthe concentrates. Suitable solid carriers are, for example, talc,titanium dioxide, pyrophyllite clay, silica, attapulgite clay,kieselguhr, limestone, calcium carbonate, bentonite, calciummontomorillonite, cottonseed husks, wheatmeal, soybean flour, pumice,wood flour, ground walnut shells, lignin and similar materials, asdescribed, for example, in CFR 180.1001. (c) & (d).

A large number of surface-active substances can advantageously be usedboth in solid and in liquid formulations, especially in thoseformulations which can be diluted with a carrier prior to use.Surface-active substances may be anionic, cationic, non-ionic orpolymeric and they may be used as emulsifiying, wetting or suspendingagents or for other purposes. Typical surface-active substances include,for example, salts of alkyl sulfates, such as diethanolammonium laurylsulfate; salts of alkylarylsulfonates, such as calciumdodecyl-benzenesulfonate; alkylphenol-alkylene oxide addition products,such as nonylphenol ethoxylate; alcohol-alkylene oxide additionproducts, such as tridecyl alcohol ethoxylate; soaps, such as sodiumstearate; salts of alkylnaphthalenesulfonates, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride, polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono- and di-alkyl phosphate esters; andalso further substances described e.g. in “McCutcheon's Detergents andEmulsifiers Annual”, MC Publishing Corp., Ridgewood, N.J., 1981.

Further adjuvants which can usually be used in pesticidal formulationsinclude crystallisation inhibitors, viscosity-modifying substances,suspending agents, dyes, anti-oxidants, foaming agents, light absorbers,mixing aids, anti-foams, complexing agents, neutralising or pH-modifyingsubstances and buffers, corrosion-inhibitors, fragrances, wettingagents, absorption improvers, micronutrients, plasticisers, glidants,lubricants, dispersants, thickeners, anti-freezes, microbiocides, andalso liquid and solid fertilisers.

The formulations may also comprise additional active substances, forexample further herbicides, herbicide safeners, plant growth regulators,fungicides or insecticides.

The compositions according to the invention can additionally include anadditive comprising an oil of vegetable or animal origin, a mineral oil,alkyl esters of such oils or mixtures of such oils and oil derivatives.The amount of oil additive used in the composition according to theinvention is generally from 0.01 to 10%, based on the spray mixture. Forexample, the oil additive can be added to the spray tank in the desiredconcentration after the spray mixture has been prepared. Preferred oiladditives comprise mineral oils or an oil of vegetable origin, forexample rapeseed oil, olive oil or sunflower oil, emulsified vegetableoil, such as AMIGO® (Rhone-Poulenc Canada Inc.), alkyl esters of oils ofvegetable origin, for example the methyl derivatives, or an oil ofanimal origin, such as fish oil or beef tallow. A preferred additivecontains, for example, as active components essentially 80% by weightalkyl esters of fish oils and 15% by weight methylated rapeseed oil, andalso 5% by weight of customary emulsifiers and pH modifiers. Especiallypreferred oil additives comprise alkyl esters of C₈-C₂₂ fatty acids,especially the methyl derivatives of C₁₂-C₁₈ fatty acids, for examplethe methyl esters of lauric acid, palmitic acid and oleic acid, beingimportant. Those esters are known as methyl laurate (CAS-111-82-0),methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9). Apreferred fatty acid methyl ester derivative is Emery® 2230 and 2231(Cognis GmbH). Those and other oil derivatives are also known from theCompendium of Herbicide Adjuvants, 5th Edition, Southern IllinoisUniversity, 2000.

The application and action of the oil additives can be further improvedby combining them with surface-active substances, such as non-ionic,anionic or cationic surfactants. Examples of suitable anionic, non-ionicand cationic surfactants are listed on pages 7 and 8 of WO 97/34485.Preferred surface-active substances are anionic surfactants of thedodecyl-benzylsulfonate type, especially the calcium salts thereof, andalso non-ionic surfactants of the fatty alcohol ethoxylate type. Specialpreference is given to ethoxylated C₁₂-C₂₂ fatty alcohols having adegree of ethoxylation of from 5 to 40. Examples of commerciallyavailable surfactants are the Genapol types (Clariant AG). Alsopreferred are silicone surfactants, especially polyalkyl-oxide-modifiedheptamethyltrisiloxanes, which are commercially available e.g. as SilwetL-77®, and also perfluorinated surfactants. The concentration ofsurface-active substances in relation to the total additive is generallyfrom 1 to 30% by weight. Examples of oil additives that consist ofmixtures of oils or mineral oils or derivatives thereof with surfactantsare Edenor ME SU®, Turbocharge® (Syngenta AG, CH) and Actipron® (BP OilUK Limited, GB).

The said surface-active substances may also be used in the formulationsalone, that is to say without oil additives.

Furthermore, the addition of an organic solvent to the oiladditive/surfactant mixture can contribute to a further enhancement ofaction. Suitable solvents are, for example, Solvesso® (ESSO) andAromatic Solvent® (Exxon Corporation). The concentration of suchsolvents can be from 10 to 80% by weight of the total weight. Such oiladditives, which may be in admixture with solvents, are described, forexample, in U.S. Pat. No. 4,834,908. A commercially available oiladditive disclosed therein is known by the name MERGE® (BASFCorporation). A further oil additive that is preferred according to theinvention is SCORE® (Syngenta Crop Protection Canada.)

In addition to the oil additives listed above, in order to enhance theactivity of the compositions according to the invention it is alsopossible for formulations of alkylpyrrolidones, (e.g. Agrimax®) to beadded to the spray mixture. Formulations of synthetic latices, such as,for example, polyacrylamide, polyvinyl compounds or poly-1-p-menthene(e.g. Bond®, Courier® or Emerald®) can also be used. Solutions thatcontain propionic acid, for example Eurogkem Pen-e-trate®, can also bemixed into the spray mixture as activity-enhancing agents.

The herbicidal formulations generally contain from 0.1 to 99% by weight,especially from 0.1 to 95% by weight, of a compound of formula I andfrom 1 to 99.9% by weight of a formulation adjuvant, which preferablyincludes from 0 to 25% by weight of a surface-active substance. Whereascommercial products will preferably be formulated as concentrates, theend user will normally employ dilute formulations.

The rate of application of the compounds of formula I may vary withinwide limits and depends upon the nature of the soil, the method ofapplication (pre- or post-emergence; seed dressing; application to theseed furrow; no tillage application etc.), the crop plant, the weed orgrass to be controlled, the prevailing climatic conditions, and otherfactors governed by the method of application, the time of applicationand the target crop. The compounds of formula I according to theinvention are generally applied at a rate of 1 to 4000 g/ha, especiallyfrom 5 to 1000 g/ha.

Preferred formulations have especially the following compositions:

(%=percent by weight):

Emulsifiable Concentrates:

active ingredient: 1 to 95%, preferably 60 to 90% surface-active agent:1 to 30%, preferably 5 to 20% liquid carrier: 1 to 80%, preferably 1 to35%

Dusts:

active ingredient:  0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9to 90%, preferably 99.9 to 99%

Suspension Concentrates:

active ingredient:  5 to 75%, preferably 10 to 50% water: 94 to 24%,preferably 88 to 30% surface-active agent:  1 to 40%, preferably 2 to30%

Wettable Powders:

active ingredient: 0.5 to 90%, preferably 1 to 80% surface-active agent:0.5 to 20%, preferably 1 to 15% solid carrier:   5 to 95%, preferably 15to 90%

Granules:

active ingredient:  0.1 to 30%, preferably 0.1 to 15% solid carrier:99.5 to 70%, preferably 97 to 85%

The following Examples further illustrate, but do not limit, theinvention.

F1. Emulsifiable concentrates a) b) c) d) active ingredient 5% 10% 25%50% calcium dodecylbenzene- 6% 8% 6% 8% sulfonate castor oil polyglycolether 4% — 4% 4% (36 mol of ethylene oxide) octylphenol polyglycol ether— 4% — 2% (7-8 mol of ethylene oxide) NMP — — 10% 20% arom. hydrocarbon85% 78% 55% 16% mixture C₉-C₁₂

Emulsions of any desired concentration can be prepared from suchconcentrates by dilution with water.

F2. Solutions a) b) c) d) active ingredient  5% 10% 50% 90%1-methoxy-3-(3-methoxy- — 20% 20% — propoxy)-propane polyethylene glycolMW 400 20% 10% — — NMP — — 30% 10% arom. hydrocarbon 75% 60% — — mixtureC₉-C₁₂

The solutions are suitable for application in the form of microdrops.

F3. Wettable powders a) b) c) d) active ingredient 5% 25%  50%  80%sodium lignosulfonate 4% — 3% — sodium lauryl sulfate 2% 3% —  4% sodiumdiisobutylnaphthalene- — 6% 5%  6% sulfonate octylphenol polyglycolether — 1% 2% — (7-8 mol of ethylene oxide) highly disperse silicic acid1% 3% 5% 10% kaolin 88%  62%  35%  —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, yielding wettablepowders which can be diluted with water to give suspensions of anydesired concentration.

F4. Coated granules a) b) c) active ingredient 0.1% 5% 15% highlydisperse silicic acid 0.9% 2% 2% inorg. carrier 99.0% 93% 83% (diameter0.1-1 mm) e.g. CaCO₃ or SiO₂

The active ingredient is dissolved in methylene chloride, the solutionis sprayed onto the carrier and the solvent is subsequently evaporatedoff in vacuo.

F5. Coated granules a) b) c) active ingredient 0.1% 5% 15% polyethyleneglycol MW 200 1.0% 2% 3% highly disperse silicic acid 0.9% 1% 2% inorg.carrier 98.0% 92% 80% (diameter 0.1-1 mm) e.g. CaCO₃ or SiO₂

The finely ground active ingredient is applied uniformly, in a mixer, tothe carrier moistened with polyethylene glycol. Non-dusty coatedgranules are obtained in this manner.

F6. Extruder granules a) b) c) d) active ingredient 0.1% 3% 5% 15%sodium lignosulfonate 1.5% 2% 3% 4% carboxymethylcellulose 1.4% 2% 2% 2%kaolin 97.0% 93% 90% 79%

The active ingredient is mixed and ground with the adjuvants and themixture is moistened with water. The resulting mixture is extruded andthen dried in a stream of air.

F7. Dusts a) b) c) active ingredient 0.1% 1% 5% talcum 39.9% 49% 35%kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active ingredient with thecarriers and grinding the mixture in a suitable mill.

F8. Suspension concentrates a) b) c) d) active ingredient   3%  10%  25% 50% ethylene glycol   5%   5%   5%   5% nonylphenol polyglycol ether —  1%   2% — (15 mol of ethylene oxide) sodium lignosulfonate   3%   3%  4%   5% carboxymethylcellulose   1%   1%   1%   1% 37% aqueousformaldehyde 0.2% 0.2% 0.2% 0.2% solution silicone oil emulsion 0.8%0.8% 0.8% 0.8% water  87%  79%  62%  38%

The finely ground active ingredient is intimately mixed with theadjuvants, yielding a suspension concentrate from which suspensions ofany desired concentration can be prepared by dilution with water.

The invention relates also to a method for the selective control ofgrasses and weeds in crops of useful plants, which comprises treatingthe useful plants or the area under cultivation or the locus thereofwith a compound of formula I.

Crops of useful plants in which the compositions according to theinvention can be used include especially cereals, cotton, soybeans,sugar beet, sugar cane, plantation crops, rape, maize and rice, and fornon-selective weed control. The term “crops” is to be understood as alsoincluding crops that have been rendered tolerant to herbicides orclasses of herbicides (for example ALS, GS, EPSPS, PPO, ACCase and HPPDinhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant e.g.to imidazolinones, such as imazamox, by conventional methods of breedingis Clearfield® summer rape (Canola). Examples of crops that have beenrendered tolerant to herbicides by genetic engineering methods includee.g. glyphosate- and glufosinate-resistant maize varieties commerciallyavailable under the trade names RoundupReady® and LibertyLink®. Theweeds to be controlled may be both monocotyledonous and dicotyledonousweeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria,Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus,Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum, Rottboellia,Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea,Chrysanthemum, Galium, Viola and Veronica.

Crops are also to be understood as being those which have been renderedresistant to harmful insects by genetic engineering methods, for exampleBt maize (resistant to European corn borer), Bt cotton (resistant tocotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).Examples of Bt maize are the Bt-176 maize hybrids of NK® (SyngentaSeeds). The Bt toxin is a protein that is formed naturally by Bacillusthuringiensis soil bacteria. Examples of toxins and transgenic plantsable to synthesise such toxins are described in EP-A-451 878, EP-A-374753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examplesof transgenic plants that contain one or more genes which code for aninsecticidal resistance and express one or more toxins are KnockOut®(maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton),NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops and theirseed material can be resistant to herbicides and at the same time alsoto insect feeding (“stacked” transgenic events). Seed can, for example,have the ability to express an insecticidally active Cry3 protein and atthe same time be glyphosate-tolerant. The term “crops” is to beunderstood as also including crops obtained as a result of conventionalmethods of breeding or genetic engineering which contain so-calledoutput traits (e.g. improved flavour, storage stability, nutritionalcontent).

Areas under cultivation are to be understood as including land where thecrop plants are already growing as well as land intended for thecultivation of those crop plants.

The compounds of formula I according to the invention can also be usedin combination with other herbicides. The following mixtures of thecompound of formula I are especially important. Preferably, in thesemixtures, the compound of the formula I is one of those compounds listedin Tables 1 to 592 below:

compound of formula I+acetochlor, compound of formula I+acifluorfen,compound of formula I+acifluorfen-sodium, compound of formulaI+aclonifen, compound of formula I+acrolein, compound of formulaI+alachlor, compound of formula I+alloxydim, compound of formula I+allylalcohol, compound of formula I+ametryn, compound of formulaI+amicarbazone, compound of formula I+amidosulfuron, compound of formulaI+aminopyralid, compound of formula I+amitrole, compound of formulaI+ammonium sulfamate, compound of formula I+anilofos, compound offormula I+asulam, compound of formula I+atrazine, formula I+aviglycine,formula I+azafenidin, compound of formula I+azimsulfuron, compound offormula I+BCPC, compound of formula I+beflubutamid, compound of formulaI+benazolin, formula I+bencarbazone, compound of formula I+benfluralin,compound of formula I+benfuresate, compound of formula I+bensulfuron,compound of formula I+bensulfuron-methyl, compound of formulaI+bensulide, compound of formula I+bentazone, compound of formulaI+benzfendizone, compound of formula I+benzobicyclon, compound offormula I+benzofenap, compound of formula I+bifenox, compound of formulaI+bilanafos, compound of formula I+bispyribac, compound of formulaI+bispyribac-sodium, compound of formula I+borax, compound of formulaI+bromacil, compound of formula I+bromobutide, formula I+bromophenoxim,compound of formula I+bromoxynil, compound of formula I+butachlor,compound of formula I+butafenacil, compound of formula I+butamifos,compound of formula I+butralin, compound of formula I+butroxydim,compound of formula I+butylate, compound of formula I+cacodylic acid,compound of formula I+calcium chlorate, compound of formulaI+cafenstrole, compound of formula I+carbetamide, compound of formulaI+carfentrazone, compound of formula I+carfentrazone-ethyl, compound offormula I+CDEA, compound of formula I+CEPC, compound of formulaI+chlorflurenol, compound of formula I+chlorflurenol-methyl, compound offormula I+chloridazon, compound of formula I+chlorimuron, compound offormula I+chlorimuron-ethyl, compound of formula I+chloroacetic acid,compound of formula I+chlorotoluron, compound of formula I+chlorpropham,compound of formula I+chlorsulfuron, compound of formula I+chlorthal,compound of formula I+chlorthal-dimethyl, compound of formulaI+cinidon-ethyl, compound of formula I+cinmethylin, compound of formulaI+cinosulfuron, compound of formula I+cisanilide, compound of formulaI+clethodim, compound of formula I+clodinafop, compound of formulaI+clodinafop-propargyl, compound of formula I+clomazone, compound offormula I+clomeprop, compound of formula I+clopyralid, compound offormula I+cloransulam, compound of formula I+cloransulam-methyl,compound of formula I+CMA, compound of formula I+4-CPB, compound offormula I+CPMF, compound of formula I+4-CPP, compound of formula I+CPPC,compound of formula I+cresol, compound of formula I+cumyluron, compoundof formula I+cyanamide, compound of formula I+cyanazine, compound offormula I+cycloate, compound of formula I+cyclosulfamuron, compound offormula I+cycloxydim, compound of formula I+cyhalofop, compound offormula I+cyhalofop-butyl, compound of formula I+2,4-D, compound offormula I+3,4-DA, compound of formula I+daimuron, compound of formulaI+dalapon, compound of formula I+dazomet, compound of formula I+2,4-DB,compound of formula I+3,4-DB, compound of formula I+2,4-DEB, compound offormula I+desmedipham, formula I+desmetryn, compound of formulaI+dicamba, compound of formula I+dichlobenil, compound of formulaI+ortho-dichlorobenzene, compound of formula I+para-dichlorobenzene,compound of formula I+dichiorprop, compound of formula I+dichlorprop-P,compound of formula I+diclofop, compound of formula I+diclofop-methyl,compound of formula I+diclosulam, compound of formula I+difenzoquat,compound of formula I+difenzoquat metilsulfate, compound of formulaI+diflufenican, compound of formula I+diflufenzopyr, compound of formulaI+dimefuron, compound of formula I+dimepiperate, compound of formulaI+dimethachlor, compound of formula I+dimethametryn, compound of formulaI+dimethenamid, compound of formula I+dimethenamid-P, compound offormula I+dimethipin, compound of formula I+dimethylarsinic acid,compound of formula I+dinitramine, compound of formula I+dinoterb,compound of formula I+diphenamid, formula I+dipropetryn, compound offormula I+diquat, compound of formula I+diquat dibromide, compound offormula I+dithiopyr, compound of formula I+diuron, compound of formulaI+DNOC, compound of formula I+3,4-DP, compound of formula I+DSMA,compound of formula I+EBEP, compound of formula I+endothal, compound offormula I+EPTC, compound of formula I+esprocarb, compound of formulaI+ethalfluralin, compound of formula I+ethametsulfuron, compound offormula I+ethametsulfuron-methyl, formula I+ethephon, compound offormula I+ethofumesate, compound of formula I+ethoxyfen, compound offormula I+ethoxysulfuron, compound of formula I+etobenzanid, compound offormula I+fenoxaprop-P, compound of formula I+fenoxaprop-P-ethyl,compound of formula I+fentrazamide, compound of formula I+ferroussulfate, compound of formula I+flamprop-M, compound of formulaI+flazasulfuron, compound of formula I+florasulam, compound of formulaI+fluazifop, compound of formula I+fluazifop-butyl, compound of formulaI+fluazifop-P, compound of formula I+fluazifop-P-butyl, formulaI+fluazolate, compound of formula I+flucarbazone, compound of formulaI+flucarbazone-sodium, compound of formula I+flucetosulfuron, compoundof formula I+fluchloralin, compound of formula I+flufenacet, compound offormula I+flufenpyr, compound of formula I+flufenpyr-ethyl, formulaI+flumetralin, compound of formula I+flumetsulam, compound of formulaI+flumiclorac, compound of formula I+flumiclorac-pentyl, compound offormula I+flumioxazin, formula I+flumipropin, compound of formulaI+fluometuron, compound of formula I+fluoroglycofen, compound of formulaI+fluoroglycofen-ethyl, formula I+fluoxaprop, formula I+flupoxam,formula I+flupropacil, compound of formula I+flupropanate, compound offormula I+flupyrsulfuron, compound of formulaI+flupyrsulfuron-methyl-sodium, compound of formula I+flurenol, compoundof formula I+fluridone, compound of formula I+fluorochloridone, compoundof formula I+fluoroxypyr, compound of formula I+flurtamone, compound offormula I+fluthiacet, compound of formula I+fluthiacet-methyl, compoundof formula I+fomesafen, compound of formula I+foramsulfuron, compound offormula I+fosamine, compound of formula I+glufosinate, compound offormula I+glufosinate-ammonium, compound of formula I+glyphosate,compound of formula I+halosulfuron, compound of formulaI+halosulfuron-methyl, compound of formula I+haloxyfop, compound offormula I+haloxyfop-P, compound of formula I+HC-252, compound of formulaI+hexazinone, compound of formula I+imazamethabenz, compound of formulaI+imazamethabenz-methyl, compound of formula I+imazamox, compound offormula I+imazapic, compound of formula I+imazapyr, compound of formulaI+imazaquin, compound of formula I+imazethapyr, compound of formulaI+imazosulfuron, compound of formula I+indanofan, compound of formulaI+iodomethane, compound of formula I+iodosulfuron, compound of formulaI+iodosulfuron-methyl-sodium, compound of formula I+ioxynil, compound offormula I+isoproturon, compound of formula I+isouron, compound offormula I+isoxaben, compound of formula I+isoxachlortole, compound offormula I+isoxaflutole, formula I+isoxapyrifop, compound of formulaI+karbutilate, compound of formula I+lactofen, compound of formulaI+lenacil, compound of formula I+linuron, compound of formula I+MAA,compound of formula I+MAMA, compound of formula I+MCPA, compound offormula I+MCPA-thioethyl, compound of formula I+MCPB, compound offormula I+mecoprop, compound of formula I+mecoprop-P, compound offormula I+mefenacet, compound of formula I+mefluidide, compound offormula I+mesosulfuron, compound of formula I+mesosulfuron-methyl,compound of formula I+mesotrione, compound of formula I+metam, compoundof formula I+metamifop, compound of formula I+metamitron, compound offormula I+metazachlor, compound of formula I+methabenzthiazuron, formulaI+methazole, compound of formula I+methylarsonic acid, compound offormula I+methyldymron, compound of formula I+methyl isothiocyanate,compound of formula I+metobenzuron, formula I+metobromuron, compound offormula I+metolachlor, compound of formula I+S-metolachlor, compound offormula I+metosulam, compound of formula I+metoxuron, compound offormula I+metribuzin, compound of formula I+metsulfuron, compound offormula I+metsulfuron-methyl, compound of formula I+MK-616, compound offormula I+molinate, compound of formula I+monolinuron, compound offormula I+MSMA, compound of formula I+naproanilide, compound of formulaI+napropamide, compound of formula I+naptalam, formula I+NDA-402989,compound of formula I+neburon, compound of formula I+nicosulfuron,formula I+nipyraclofen, formula I+n-methyl glyphosate, compound offormula I+nonanoic acid, compound of formula I+norflurazon, compound offormula I+oleic acid (fatty acids), compound of formula I+orbencarb,compound of formula I+orthosulfamuron, compound of formula I+oryzalin,compound of formula I+oxadiargyl, compound of formula I+oxadiazon,compound of formula I+oxasulfuron, compound of formula I+oxaziclomefone,compound of formula I+oxyfluorfen, compound of formula I+paraquat,compound of formula I+paraquat dichloride, compound of formulaI+pebulate, compound of formula I+pendimethalin, compound of formulaI+penoxsulam, compound of formula I+pentachlorophenol, compound offormula I+pentanochlor, compound of formula I+pentoxazone, compound offormula I+pethoxamid, compound of formula I+petrolium oils, compound offormula I+phenmedipham, compound of formula I+phenmedipham-ethyl,compound of formula I+picloram, compound of formula I+picolinafen,compound of formula I+pinoxaden, compound of formula I+piperophos,compound of formula I+potassium arsenite, compound of formulaI+potassium azide, compound of formula I+pretilachlor, compound offormula I+primisulfuron, compound of formula I+primisulfuron-methyl,compound of formula I+prodiamine, compound of formula I+profluazol,compound of formula I+profoxydim, formula I+prohexadione-calcium,compound of formula I+prometon, compound of formula I+prometryn,compound of formula I+propachlor, compound of formula I+propanil,compound of formula I+propaquizafop, compound of formula I+propazine,compound of formula I+propham, compound of formula I+propisochlor,compound of formula I+propoxycarbazone, compound of formulaI+propoxycarbazone-sodium, compound of formula I+propyzamide, compoundof formula I+prosulfocarb, compound of formula I+prosulfuron, compoundof formula I+pyraclonil, compound of formula I+pyraflufen, compound offormula I+pyraflufen-ethyl, formula I+pyrasulfotole, compound of formulaI+pyrazolynate, compound of formula I+pyrazosulfuron, compound offormula I+pyrazosulfuron-ethyl, compound of formula I+pyrazoxyfen,compound of formula I+pyribenzoxim, compound of formula I+pyributicarb,compound of formula I+pyridafol, compound of formula I+pyridate,compound of formula I+pyriftalid, compound of formula I+pyriminobac,compound of formula I+pyriminobac-methyl, compound of formulaI+pyrimisulfan, compound of formula I+pyrithiobac, compound of formulaI+pyrithiobac-sodium, formula I+pyroxasulfone (KIH-485), formulaI+pyroxulam, compound of formula I+quinclorac, compound of formulaI+quinmerac, compound of formula I+quinoclamine, compound of formulaI+quizalofop, compound of formula I+quizalofop-P, compound of formulaI+rimsulfuron, compound of formula I+sethoxydim, compound of formulaI+siduron, compound of formula I+simazine, compound of formulaI+simetryn, compound of formula I+SMA, compound of formula I+sodiumarsenite, compound of formula I+sodium azide, compound of formulaI+sodium chlorate, compound of formula I+sulcotrione, compound offormula I+sulfentrazone, compound of formula I+sulfometuron, compound offormula I+sulfometuron-methyl, compound of formula I+sulfosate, compoundof formula I+sulfosulfuron, compound of formula I+sulfuric acid,compound of formula I+tar oils, compound of formula I+2,3,6-TBA,compound of formula I+TCA, compound of formula I+TCA-sodium, formulaI+tebutam, compound of formula I+tebuthiuron, formula I+tefuryltrione,compound of formula 1+tembotrione, compound of formula I+tepraloxydim,compound of formula I+terbacil, compound of formula I+terbumeton,compound of formula I+terbuthylazine, compound of formula I+terbutryn,compound of formula I+thenylchlor, compound of formula I+thiazafluoron,compound of formula I+thiazopyr, compound of formula I+thifensulfuron,compound of formula I+thiencarbazone, compound of formulaI+thifensulfuron-methyl, compound of formula I+thiobencarb, compound offormula I+tiocarbazil, compound of formula I+topramezone, compound offormula I+tralkoxydim, compound of formula I+triallate, compound offormula I+triasulfuron, compound of formula I+triaziflam, compound offormula I+tribenuron, compound of formula I+tribenuron-methyl, compoundof formula I+tricamba, compound of formula I+triclopyr, compound offormula I+trietazine, compound of formula I+trifloxysulfuron, compoundof formula I+trifloxysulfuron-sodium, compound of formula I+trifluralin,compound of formula I+triflusulfuron, compound of formulaI+triflusulfuron-methyl, compound of formula I+trihydroxytriazine,compound of formula I+trinexapac-ethyl, compound of formulaI+tritosulfuron, compound of formulaI+[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]aceticacid ethyl ester (CAS RN 353292-31-6), compound of formulaI+4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]-bicyclo[3.2.1]oct-3-en-2-one(CAS RN 352010-68-5), and compound of formulaI+4-hydroxy-3-[[2-(3-methoxypropyl)-6-(difluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one.

The compounds of formula I according to the invention can also be usedin combination with safeners. Preferably, in these mixtures, thecompound of the formula I is one of those compounds listed in Tables 1to 592 below. The following mixtures with safeners, especially, comeinto consideration:

compound of formula I+cloquintocet-mexyl, compound of formulaI+cloquintocet acid and salts thereof, compound of formulaI+fenchlorazole-ethyl, compound of formula I+fenchlorazole acid andsalts thereof, compound of formula I+mefenpyr-diethyl, compound offormula I+mefenpyr diacid, compound of formula I+isoxadifen-ethyl,compound of formula I+isoxadifen acid, compound of formula I+furilazole,compound of formula I+furilazole R isomer, compound of formulaI+benoxacor, compound of formula I+dichlormid, compound of formulaI+AD-67, compound of formula I+oxabetrinil, compound of formulaI+cyometrinil, compound of formula I+cyometrinil Z-isomer, compound offormula I+fenclorim, compound of formula I+cyprosulfamide, compound offormula I+naphthalic anhydride, compound of formula I+flurazole,compound of formulaI+N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]-benzenesulfonamide,compound of formula I+CL 304,415, compound of formula I+dicyclonon,compound of formula I+fluxofenim, compound of formula I+DKA-24, compoundof formula I+R-29148 and compound of formula I+PPG-1292. A safeningeffect can also be observed for the mixtures compound of the formulaI+dymron, compound of the formula I+MCPA, compound of the formulaI+mecopropand compound of the formula I+mecoprop-P.

The above-mentioned safeners and herbicides are described, for example,in the Pesticide Manual, Twelfth Edition, British Crop ProtectionCouncil, 2000, or other readily available resources. R-29148 isdescribed, for example by P. B. Goldsbrough et al., Plant Physiology,(2002), Vol. 130 pp. 1497-1505 and references, PPG-1292 is known fromWO09211761 andN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide isknown from EP365484.

Depending on the use, the herbicidal compositions according to thepresent invention may contain a compound of the formula I, a furtherherbicide as mixing partner and a safener, as mentioned above.

The herbicidal compositions according to the invention are suitable forall methods of application customary in agriculture, such as, forexample, pre-emergence application, post-emergence application and seeddressing. Depending upon the intended use, the safeners can be used forpretreating the seed material of the crop plant (dressing the seed orseedlings) or introduced into the soil before or after sowing, followedby the application of the (unsafened) compound of the formula I,optionally in combination with a co-herbicide. It can, however, also beapplied alone or together with the herbicide before or after emergenceof the plants. The treatment of the plants or the seed material with thesafener can therefore take place in principle independently of the timeof application of the herbicide. The treatment of the plant bysimultaneous application of herbicide and safener (e.g. in the form of atank mixture) is generally preferred. The rate of application of safenerrelative to herbicide is largely dependent upon the mode of application.In the case of field treatment, generally from 0.001 to 5.0 kg ofsafener/ha, preferably from 0.001 to 0.5 kg of safener/ha, are applied.In the case of seed dressing, generally from 0.001 to 10 g of safener/kgof seed, preferably from 0.05 to 2 g of safener/kg of seed, are applied.When the safener is applied in liquid form, with seed soaking, shortlybefore sowing, it is advantageous to use safener solutions which containthe active ingredient in a concentration of from 1 to 10 000 ppm,preferably from 100 to 1000 ppm.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of compound of formula I with the mixing partner).

The following examples illustrate the invention further but do not limitthe invention.

Those skilled in the art will appreciate that certain compoundsdescribed below are β-ketoenols, and as such may exist as a singletautomer or as a mixture of keto-enol and diketone tautomers, asdescribed, for example by J. March, Advanced Organic Chemistry, thirdedition, John Wiley and Sons. The compounds shown below, and in Table T1and P1, are drawn as an arbitrary single enol tautomer, but it should beinferred that this description covers both the diketone form and anypossible enols which could arise through tautomerism. Furthermore, someof the compounds shown below, and in Table T1 and P1, are drawn assingle enantiomers for the purposes of simplicity, but unless specifiedas single enantiomers, these structures should be construed asrepresenting a mixture of enantiomers. Additionally, some of thecompounds can exist as diastereoisomers, and it should be inferred thatthese can be present as a mixture of diastereoisomers or as any possiblesingle diastereoisomer. Within the detailed experimental section thediketone tautomer is chosen for naming purposes, even if the predominanttautomer is the enol form.

PREPARATION EXAMPLES Example 1 Preparation of6-[5-(4-chloro-3-methylphenyl)-2-methylthiophen-3-yl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione(Compound T4 in Table T1)

Step 1 Preparation of5-(5-bromothiophen-2-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

To a solution of 5-bromothiophen-2-ylmethanol (6.76 g, 35 mmol) intetrahydrofuran (100 ml) at 0° C. is added, carefully, sodium hydride,60% dispersion in mineral oil, (1.2 g, 30 mmol over a period of 10minutes. The reaction is allowed to warm to room temperature and stirredfor a further hour. 5-Chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione(5.02 mg, 25 mmol) is then added in one portion and the reaction mixtureis allowed to stir at room temperature for 17 hours. The reaction isconcentrated in vacuo and purified by flash chromatography on silica gelto give the desired compound as a white solid (4.45 g)

Step 2 Preparation of6-[5-(4-chloro-3-methylphenyl)-2-methylthiophen-3-yl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione

A mixture of5-(5-bromothiophen-2-ylmethoxy)-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione(107 mg, 0.3 mmol), 4-chloro-m-tolyl boronic acid (60 mg, 0.35 mmol),palladium acetate (4 mg, 0.015 mmol), Ru-Phos (14 mg, 0.03 mmol) andcaesium carbonate (130 mg, 0.4 mmol) in toluene (2 ml) is heated to 180°C. for 30 minutes under microwave irradiation and the resulting materialis purified by flash chromatography on silica gel to give6-[5-(4-chloro-3-methylphenyl)-2-methylthiophen-3-yl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione.

Example 2 Preparation of6-[2-(2,5-dichlorophenyl)-5-methylthiazol-4-yl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione(Compound T10 in Table T1)

Step 1 Preparation of5-(2-bromothiazol-5-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

To a suspension of sodium hydride, 60% dispersion in mineral oilsolution (1.6 g, 40 mmol) in tetrahydrofuran (50 ml) is added a solutionof (2-bromothiazol-5-yl)methanol (6.75 g, 35 mmol) in tetrahydrofuran(50 ml) at 0° C. A solution of5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (7.0 g, 35 mmol) intetrahydrofuran (50 ml) is then added and the reaction mixture is heatedto reflux for 18 hours. The reaction mixture is poured into water,acidified to pH4 with dilute aqueous hydrochloric acid and extractedwith ethyl acetate (4×50 ml). The combined organic layers are dried overanhydrous magnesium sulfate, filtered and the filtrate is evaporated toa brown oil. The crude product is purified by flash chromatography onsilica gel to give5-(2-bromothiazol-5-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione(6.75 g).

Step 2 Preparation of6-[2-(2,5-dichlorophenyl)-5-methylthiazol-4-yl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione

2,5-dichlorophenylboronic acid (266 mg, 1.39 mmol),5-(2-bromothiazol-5-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione(250 mg, 0.7 mmol), toluene (3 ml), caesium carbonate (310 mg, 0.95mmol) and[1,3-bis(2,6-diisopropyl)imidazol-2-ylidene](3-chloropyridyl)palladiumII dichloride (60 mg, 0.12 mmol) are mixed together in a microwave vialand heated to 150° C. for 30 min under microwave irradiation. Thereaction mixture is cooled, filtered, evaporated and purified by flashchromatography on silica gel to give an orange oil. The oil is dissolvedin diglyme (3 ml) and 1-butyl-3-methyl imidazoliumbis(trifluoromethylsulfonyl)imide (0.1 ml) and heated under microwaveirradiation at 210° C. for 30 min. The reaction mixture is cooled toroom temperature, the solvent is evaporated under reduced pressure andthe residue is purified by flash chromatography on silica gel to give6-[2-(2,5-dichlorophenyl)-5-methylthiazol-4-yl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione.

Example 3 Preparation of4-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione(Compound T11 in Table T1)

Step 1 Preparation of 5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one

To a suspension of 2,2,6,6-tetramethylpyran-3,5-dione (741 mg, 4.35mmol) in chloroform (10 ml) is added phosphorus pentachloride (454 mg,2.18 mmol), and the reaction is heated to reflux for 5 hours. Silica gelis added to the cooled crude reaction mixture, the solvent is evaporatedunder reduced pressure and the residue is purified by flashchromatography on silica gel to give5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one (349 mg).

Step 2 Preparation of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol

To a stirred solution of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanone(2.38 g, 10 mmol) in methanol (20 ml) at 0° C. is added sodiumborohydride (379 mg, 10.5 mmol) in one portion. The resultant solutionis allowed to warm to room temperature, and is then stirred at roomtemperature for 3 hours. The reaction is quenched with saturated aqueousammonium chloride solution (200 ml) and extracted with chloroform (200ml). The organic layer is dried over anhydrous magnesium sulfate andconcentrated in vacuuo to give desired product as a brown solid (2.32 g)

Step 3 Preparation of5-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}-2,2,6,6-tetramethyl-6H-pyran-3-one

To a solution of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol (335 mg, 1.4mmol) in anhydrous tetrahydrofuran (5 ml) under nitrogen is added sodiumhydride, 60% dispersion in mineral oil, (48 mg, 1.2 mmol) and theresulting yellow suspension is allowed to stir at room temperature for 1hour. A solution of 5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one (189 mg,1 mmol) in anhydrous tetrahydrofuran (2 ml) is then added and reactionis allowed to stir at room temperature for 17 hours. The crude reactionmixture is purified by flash chromatography on silica gel to give5-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}-2,2,6,6-tetramethyl-6H-pyran-3-one(288 mg).

Step 4 Preparation of4-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione

To a solution of5-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}-2,2,6,6-tetramethyl-6H-pyran-3-one(270 mg, 0.69 mmol) in 1,2-dimethoxyethane (2 ml) is added1-butyl-methyl imidazolium bis(trifluoromethylsulphonyl)imide (0.1 ml)and the solution heated to 210° C. for 30 minutes under microwaveirradiation. The crude reaction mixture is purified by flashchromatography on silica gel to give4-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione.

Example 4 Preparation of5-[2-(4-chlorophenyl)-5-methylselenazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione(Compound T16 in Table T1)

Step 1 Preparation of 2-(4-chlorophenyl)selenazole-5-carbaldehyde

To a suspension of 4-chloroselenobenzamide (219 mg, 1 mmol) and2-chloromalonaldehyde (160 mg, 1.5 mmol) in 1,2-dimethoxyethane (1.5 ml)is added magnesium carbonate (42 mg, 0.5 mmol) and the resulting mixtureis stirred at 60° C. under an atmosphere of nitrogen for 3 hours. Thecrude reaction mixture is then filtered through a plug of silica andwashed with ethyl acetate, and filtrate is concentrated to give a brownsolid. The crude product is purified by flash chromatography on silicagel to give 2-(4-chloro-phenyl)selenazole-5-carbaldehyde (162 mg).

Step 2 Preparation of [2-(4-chlorophenyl)selenazol-5-yl]methanol

To a suspension of 2-(4-chlorophenyl)selenazole-5-carbaldehyde (130 mg,0.48 mmol) in methanol (5 ml) is added sodium borohydride (19 mg, 0.5mmol) at 0° C. The reaction mixture is stirred at 0° C. for 0.5 h. Thereaction mixture is quenched with aqueous saturated ammonium chloridesolution (10 ml), and extracted with dichloromethane (3×25 ml). Thecombined organic extracts are dried over anhydrous magnesium sulfate,filtered and the filtrate is evaporated to dryness to give[2-(4-chlorophenyl)selenazol-5-yl]methanol (127 mg).

Step 3 Preparation of5-[2-(4-chlorophenyl)selenazol-5-ylmethoxy]-2,2,6,6-tetramethyl-6H-pyran-3-one

To a solution of [2-(4-chlorophenyl)selenazol-5-yl]methanol (300 mg, 1.1mmol) in dry tetrahydrofuran (5 ml) under an atmosphere of nitrogen isadded, in one portion, the sodium hydride (44 mg, 1.1 mmol). Thereaction mixture is stirred for 5 minutes at room temperature and5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one (208 mg, 1.1 mmol) is addedin one portion. The reaction mixture is stirred at room temperatureovernight. Silica gel is added to the crude reaction mixture, and thesolvent is evaporated under reduced pressure. The residue is purified byflash chromatography on silica gel to give5-[2-(4-chlorophenyl)selenazol-5-ylmethoxy]-2,2,6,6-tetramethyl-6H-pyran-3-one(261 mg).

Step 4 Preparation of5-[2-(4-chlorophenyl)-5-methylselenazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione

5-[2-(4-chlorophenyl)selenazol-5-ylmethoxy]-2,2,6,6-tetramethyl-6H-pyran-3-one(239 mg, 0.56 mmol) is placed in a microwave vial and dissolved indiethylene glycol dimethyl ether (8 ml). 1-Butyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide (0.1 ml) is added and the reactionmixture is heated at 210° C. for 30 minutes under microwave irradiation.Silica gel is added to the crude reaction mixture, the solvent isevaporated under reduced pressure and the residue is purified by flashchromatography on silica gel to give5-[2-(4-chlorophenyl)-5-methylselenazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione.

Example 5 Preparation of3-[2-(4-chloro-phenyl)-5-ethyl-thiazol-4-yl]-1-methyl-8-oxa-bicyclo[3.2.1]-octane-2,4-dione(Compound T50 in Table T1)

Step 1 Preparation of(1R*,5S*-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene

Pentachlorocyclopropane (100 g, 0.467 mol) is added to a suspension ofpotassium hydroxide (31.4 g, 0.56 mol) in 1,4-dioxane (3600 ml) and themixture is stirred at room temperature for 30 minutes and then heated to65° C. for a further 30 minutes. 2-Methylfuran (38.36 g, 0.467 mol) isadded to the reaction mixture, the temperature is raised to 85-90° C.and the mixture is stirred for 16 hours. The reaction mixture is cooledto room temperature, filtered through a plug of diatomaceous earth andthe filtrate evaporated in vacuo to give(1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene(83 g), used without further purification in the next step.

Step 2 Preparation of(1R*,5S*)-3,4-dichloro-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one

Silver nitrate (166 g, 0.982 mol) is added to a stirred mixture of(1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene(83 g, 0.491 mol), acetone (1500 ml) and water (1500 ml) and the mixtureis heated at 65° C. for 16 hours. The reaction mixture is cooled to roomtemperature, and a saturated solution of aqueous sodium bicarbonate isadded to adjust the pH to 7-8. The mixture is filtered through a plug ofdiatomaceous earth, and the filtrate is concentrated in vacuo to removemost of the acetone. The aqueous mixture is extracted with ethyl acetate(3×500 ml) and the organic extracts are combined, dried over anhydroussodium sulfate, filtered and the filtrate is evaporated. The residue ispurified by flash column chromatography on silica gel to give(1R*,5S*)-3,4-dichloro-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one(29.5 g) as a yellow oil.

Step 3 Preparation of3-chloro-1-methyl-4-oxo-spiro(1,3-dioxolane-2,2′-[8]oxa-bicyclo[3.2.1]oct-6-ene)

Sodium (4.41 g, 0.204 mol) is added cautiously to ethylene glycol (99.75g) and the mixture is stirred at 35-40° C. under an atmosphere ofnitrogen until the sodium is completely dissolved. A solution of(1R*,5S*)-3,4-dichloro-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one(28 g, 0.136 mol) in tetrahydrofuran (200 ml) is added dropwise over 30minutes, and once the addition is complete, the mixture is stirred for90 minutes at room temperature. The reaction mixture is neutralised byaddition of 10% aqueous sodium dihydrogen phosphate, and extracted withethyl acetate (3×100 ml). The organic extracts are combined, dried overanhydrous sodium sulfate, filtered and the filtrate is evaporated. Theresidue is purified by flash column chromatography on silica gel to give3-chloro-1-methyl-4-oxo-spiro(1,3-dioxolane-2,2′-[8]oxabicyclo[3.2.1]oct-6-ene)(24.5 g) as a gum.

Step 4 Preparation of(1R*,5S*)-1-methyl-4-oxo-spiro(1,3-dioxolane-2,2′-[8]-oxa-bicyclo[3.2.1]oct-6-ene)

Zinc powder (13.88 g, 0.212 mol) is added to a solution of3-chloro-1-methyl-4-oxo-spiro(1,3-dioxolane-2,2′-[8]oxabicyclo[3.2.1]oct-6-ene)(24.5 g, 0.016 mol) in acetic acid (122.5 ml) and the reaction mixturestirred at room temperature for 24 hours. The mixture is diluted withwater (612.5 ml) and extracted with ethyl acetate (3×150 ml). Theorganic extracts are combined, dried over anhydrous sodium sulfate,filtered and the filtrate is evaporated to give(1R*,5S*)-1-methyl-4-oxo-spiro(1,3-dioxolane-2,2′-[8]oxabicyclo[3.2.1]oct-6-ene)(20 g) as a yellow oil, used without further purification in the nextstep.

Step 5 Preparation of(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione

Hydrochloric acid (50 ml) is added, in three portions, to a mixture of(1R*,5S*)-1-methyl-4-oxo-spiro(1,3-dioxolane-2,2′-[8]oxabicyclo[3.2.1]oct-6-ene)(20 g, 0.102 mol) in acetone (500 ml) and water (250 ml) and thereaction mixture is stirred at 65-70° C. for 48 hrs. The mixture iscooled to room temperature, most of the acetone is removed byevaporation under reduced pressure and the resulting aqueous solution isextracted with ethyl acetate (3×100 ml). The organic extracts arecombined, dried over anhydrous sodium sulfate, filtered and the filtrateis evaporated. The residue is purified by flash column chromatography onsilica gel to give(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione (10.0 g) as ayellow oil.

Step 6 Preparation of(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione

To a solution of(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione (12.0 g, 0.079mol) in ethyl acetate (100 ml) is added 10% palladium on carbon (2.4 g),followed by stirring under a 1 bar hydrogen atmosphere for 24 hours. Thereaction mixture is then filtered through diatomaceous earth andconcentrated to give a crude product which is purified by flashchromatography (hexane/ethyl acetate) to afford(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione (6.90 g) as paleyellow solid.

Step 7 Preparation of4-chloro-1-methyl-8-oxa-bicyclo[3.2.1]oct-3-en-2-one

To a solution of 1-methyl-8-oxa-bicyclo[3.2.1]octane-2,4-dione (175 mg,1.14 mmol) in chloroform (2 ml) is added, under N₂, in one portion, thephosphorous pentachloride (135 mg, 0.65 mmol). The reaction mixture isstirred for reflux for 5 hours. Silica gel is added to the cooled crudereaction mixture, the solvent is evaporated under reduced pressure andthe residue is purified by flash chromatography on silica gel to give4-chloro-1-methyl-8-oxa-bicyclo[3.2.1]oct-3-en-2-one (93 mg).

Step 8 Preparation of4-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}-1-methyl-8-oxabicyclo[3.2.1]oct-3-en-2-one

To a solution of 1-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol (129 mg, 0.54mmol) and 4-chloro-1-methyl-8-oxabicyclo[3.2.1]oct-3-en-2-one (93 mg,0.54 mmol) in dry THF (5 ml) is added in one portion the sodium hydride,60% dispersion in mineral oil, (21 mg, 0.54 mmol). The reaction mixtureis stirred at room temperature overnight. Silica gel is added to thecrude reaction mixture, and the solvent is evaporated under reducedpressure. The residue is purified by flash chromatography on silica gelto give4-{1-[2-(4-Chlorophenyl)thiazol-5-yl]-ethoxy}-1-methyl-8-oxabicyclo[3.2.1]oct-3-en-2-one(160 mg).

Step 9 Preparation of3-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione

4-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}-1-methyl-8-oxabicyclo[3.2.1]oct-3-en-2-one(160 mg, 0.42 mmol) is placed in a microwave vial and dissolved indiethylene glycol dimethyl ether (5 ml). 1-Butyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide (0.1 ml) is added and the reactionmixture is heated at 230° C. for 30 minutes under microwave irradiation.Silica gel is added to the crude reaction mixture, the solvent isevaporated under reduced pressure and the residue is purified by flashchromatography on silica gel to give3-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione.

Example 6 Preparation of4-[2-(4-chlorophenyl)-5-methylthiazol-4-yl]-2,2,6,6-tetramethylthiopyran-3,5-dione(Compound T81 in Table T1)

Step 1 Preparation of [2-(4-chlorophenyl)thiazol-5-yl]methanol

To a suspension of 2-(4-chlorophenyl)thiazole-5-carbaldehyde (3.26 g,14.6 mmol) in methanol (50 ml) is added the sodium borohydride (568 mg,15 mmol) portionwise at room temperature. The reaction mixture isstirred at room temperature for 2 h. The reaction mixture is quenchedwith 50 ml of an aqueous saturated solution of ammonium chloride,extracted with dichloromethane (2×100 ml). The combined organic extractsare dried with magnesium sulphate, filtered and evaporated to dryness togive [2-(4-chlorophenyl)thiazol-5-yl]methanol (3.24 g).

Step 2 Preparation of 5-chloromethyl-2-(4-chlorophenyl)thiazole

To a suspension of [2-(4-chlorophenyl)thiazol-5-yl]methanol (3.24 g,14.3 mmol) in dichloromethane (40 ml) is added dropwise the thionylchloride (1.3 ml, 18 mmol) at room temperature under nitrogen. Thereaction mixture is stirred at room temperature for 4 hours. Silica gelis added to the crude reaction mixture, the solvent is evaporated underreduced pressure and the residue is purified by flash chromatography onsilica gel to give 5-chloromethyl-2-(4-chlorophenyl)thiazole (3.24 g)

Step 3 Preparation of5-[2-(4-chlorophenyl)thiazol-4-ylmethoxy]-2,2,6,6-tetramethyl-6H-thiopyran-3-one

To a suspension of 2,2,6,6-tetramethylthiopyran-3,5-dione (745 mg, 4mmol) in acetone (30 ml) is added the potassium carbonate (2.07 g, 15mmol) in one portion. The reaction mixture is stirred at roomtemperature for 5 minutes and the 2-chloro-5-chloromethylthiazole (977mg, 4 mmol) is added in one portion. The reaction mixture is thereforeheated to reflux overnight. The cooled reaction mixture is diluted with50 ml of 2N aq. NaOH, 50 ml of water and extracted with EtOAc (3×75 ml).The combined organic layers are dried over magnesium sulphate, filteredand evaporated under reduced pressure. The crude product is purified byflash chromatography to give5-[2-(4-chlorophenyl)thiazol-4-ylmethoxy]-2,2,6,6-tetramethyl-6H-thiopyran-3-one(461 mg).

Step 4 Preparation of4-[2-(4-chlorophenyl)-5-methylthiazol-4-yl]-2,2,6,6-tetramethylthiopyran-3,5-dione

5-[2-(4-Chlorophenyl)thiazol-4-ylmethoxy]-2,2,6,6-tetramethyl-6H-thiopyran-3-one

(450 mg, 1.14 mmol) is placed in a microwave vial and dissolved indiethylene glycol dimethyl ether (15 ml). 1-Butyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide (0.1 ml) is added and the reactionmixture is heated at 230° C. for 30 minutes under microwave irradiation.Silica gel is added to the crude reaction mixture, the solvent isevaporated under reduced pressure and the residue is purified by flashchromatography on silica gel to give4-[2-(4-chlorophenyl)-5-methylthiazol-4-yl]-2,2,6,6-tetramethylthiopyran-3,5-dione.

Example 7 Preparation of4-[2-(4-chlorophenyl)-5-methylpyrimidin-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione(Compound T71 in Table T1)

A microwave vial is charged with4-chloro-2-(4-chlorophenyl)-5-methylpyrimidine (239 mg, 1 mmol),2,2,6,6-tetramethyl-pyran-3,5-dione (170 mg, 1 mmol), palladium acetate(12 mg, 0.05 mmol), X-Phos (48 mg, 0.1 mmol) and potassium phosphate(424 mg, 2 mmol). 1,2-dimethoxyethane (3 ml) is added and the reactionheated to 150° C., with stirring, for 30 minutes. Silica gel is added tothe crude reaction mixture, the solvent is evaporated under reducedpressure and the residue is purified by flash chromatography on silicagel to give4-[2-(4-chlorophenyl)-5-methylpyrimidin-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione.

Additional compounds in Table T1 below are prepared by similar methodsusing appropriate starting materials.

Where more than one tautomer or rotational conformer is observed in theproton NMR spectrum, the data shown below are for the mixture of isomersand conformers.

TABLE T1 Compound ¹H nmr (CDCl₃ unless stated) or Number Structure otherphysical data T1

δ ppm 1.50 (s, 12H) 2.33 (s, 3H) 7.43 (m, 2H) 7.77 (mult, 2H) T2

δ ppm 1.39 (s, 6H) 1.52 (s, 6H) 2.49 (s, 3H) 8.08 (s (br), 1H) 8.30 (s,1H) T3

δ ppm 1.43 (s, 6H) 1.54 (s, 6H) 2.29 (s, 3H) 3.99 (s, 3H) 6.11 (s, 1H)6.75 (s, 1H) 7.03 (s, 1H) T4

δ ppm 1.44 (s, 6H) 1.55 (s, 6H) 2.29 (s, 3H) 2.39 (s, 3H) 7.00 (s, 1H)7.31 (m, 2H) 7.41 (m, 1H) T5

δ ppm 1.44 (s, 6H) 1.55 (s, 6H) 2.30 (s, 3H) 6.11 (s, 1H) 7.01 (s, 1H)7.33 (m, 2H) 7.47 (m, 2H) T6

δ ppm 1.33 (t, 3H) 1.50 (s, 12H) 2.71 (q, 2H) 7.44 (m, 2H) 7.80 (m, 2H)T7

δ ppm 1.50 (s, 12H), 2.32 (s, 3H), 2.41 (s, 3H), 7.26 (d, 2H), 7.73 (d,2H) T8

δ ppm 1.50 (s, 12H), 2.32 (s, 3H), 7.15 (m, 2H), 7.83 (m, 2H) T9

δ ppm 1.50 (s, 12H) 2.35 (s, 3H) 7.28-7.26 (m, 2H) 7.99 (m, 1H) 13.40 (s(br), 1H) T10

δ ppm 1.51 (s, 12H) 2.36 (s, 3H) 7.34 (dd, 1H) 7.46 (d, 1H) 7.95 (d, 1H)13.11 (s (br), 1H) T11

δ ppm 1.33 (t, 3H) 1.56 (s, 12H) 2.82 (q, 2H) 7.42 (m, 2H) 7.78 (m, 2H)T12

δ ppm 1.53 (s, 6H) 1.65 (s, 6H) 2.34 (s, 3H) 5.96 (s, 1H) 7.06 (s, 1H)7.37 (m, 2H) 7.52 (m, 2H) T13

δ ppm 1.56 (s, 12H) 2.41 (s, 3H) 7.42 (m, 2H) 7.76 (m, 2H) T14

δ ppm 1.37 (s, 3H) 1.42 (s, 6H) 1.51 (s, 3H) 1.92 (s, 3H) 3.66 (dd, 1H)4.49 (dd, 1H) 7.39 (s, 1H) T15

δ ppm 1.55 (s (br), 12H) 2.42 (s, 3H) 7.60 (dd, 1H) 7.93 (dd, 1H) 8.11(d, 1H) T16

δ ppm 1.56 (s, 12H) 2.45 (s, 3H) 7.21 (m, 2H) 7.41 (m, 2H) T17

δ ppm 1.56 (s, 12H) 2.40 (s, 3H) 7.58 (m, 2H) 7.70 (m, 2H) T18

δ ppm 1.56 (s (br), 12H) 2.42 (s, 3H) 7.43 (d, 1H) 8.08 (dd, 1H) 8.83 (d1H) T19

δ ppm 1.57 (s, 12H) 2.45 (s, 3H) 7.69 (m, 2H) 8.72 (m, 2H) T20

δ ppm 1.49 (s (br), 6H) 1.61 (s (br), 6H) 2.31 (s, 3H) 3.92 (s, 3H) 7.15(s, 1H) 7.61 (m, 2H) 8.02 (m, 2H) T21

δ ppm 1.56 (s, 12H) 2.43 (s, 3H) 7.26 (m, 2H) 7.96 (m, 1H) T22

δ ppm 1.53-1.61 (m, 12H) 2.41 (s, 3H) 7.47 (m, 1H) 7.55 (m, 1H) 7.62 (m,1H) T23

δ ppm 1.56 (s, 12H) 2.41 (s, 3H) 7.52 (d, 1H) 7.65 (dd, 1H) 7.91 (d, 1H)T24

δ ppm 1.49 (s, 6H) 1.60 (s, 6H) 2.34 (s, 3H) 6.31 (s, br, 1H) 7.06 (m,1H) 7.31 (s, 1H) 7.41 (m, 2H) 7.59 (m, 2H) T25

δ ppm 1.44 (s, 6H) 1.57 (s, 6H) 2.29 (s, 3H) 6.21 (s, br, 1H) 6.95 (s,1H) 7.07 (m, 2H) 7.51 (m, 2H) T26

δ ppm 1.44 (s, 6H) 1.55 (s, 6H) 2.28 (s, 3H) 3.83 (s, 3H) 6.27 (s, br,1H) 6.89 (d, 2H) 6.90 (s, 1H) 7.48 (d, 2H) T27

δ ppm 1.51 (s (br), 12H) 2.32 (s, 3H) 7.12 (s, 1H) 7.63 (m, 4H) T28

δ ppm 1.44 (s, 6H) 1.56 (s, 6H) 2.30 (s, 3H) 2.54 (s, 3H) 7.04 (s, 1H)7.12 (d, 1H) 7.57 (d, 1H) T29

δ ppm 1.43 (s, 6H) 1.54 (s, 6H) 2.27 (s, 3H) 6.19 (s, 1H) 6.79 (m, 2H)6.93 (m, 3H) 7.35-7.45 (m, 2H) T30

δ ppm 1.50 (s, 12H) 2.29 (s, 3H) 3.91 (s, 3H) 6.89 (m, 2H) 7.18 (m, 1H)7.57 (d, 1H) T31

δ ppm 1.46 (s, 6H) 1.54 (s, 6H) 2.33 (s, 3H) 6.99 (s, 1H) 7.95 (m, 2H)8.15 (m, 2H) 8.91 (m, 1H) 9.50 (m, 1H) T32

δ ppm 1.50 (s, 12H) 2.30 (s, 3H) 4.07 (s, 3H) 4.14 (s, 3H) 7.14 (s, 1H)8.53 (s, 1H) T33

δ ppm 1.44 (s, 6H) 1.54 (s, 6H) 2.27 (s, 3H) 4.28 (m, 4H) 6.22 (s, 1H)6.86 (m, 2H) 7.03 (m, 2H) T34

δ ppm 1.42 (s, 6H) 1.50 (s, 6H) 2.31 (s, 3H) 6.88 (m, 1H) 7.05 (s, 1H)7.13 (m, 1H) 7.38 (m, 1H) 7.46 (m, 1H) T35

δ ppm 1.44 (s, 6H) 1.56 (s, 6H) 2.30 (s, 3H) 6.16 (s, br, 1H) 7.03 (s,1H) 7.36 (dd, 1H) 7.43 (d, 1H) 7.63 (d, 1H) T36

δ ppm 1.44 (s, 6H) 1.56 (s, 6H) 2.31 (s, 3H) 2.36 (s, 3H) 2.51 (s, 3H)6.18 (s (br), 1H) 6.73 (s, 1H) T37

δ ppm 1.45 (s, 6H) 1.59 (s, 6H) 2.29 (s, 3H) 4.04 (s, 3H) 7.00 (s, 1H)8.45 (s, 2H) T38

δ ppm 1.44 (s, 6H) 1.55 (s, 6H) 2.29 (s, 3H) 3.90 (s, 3H) 6.20 (s, br,1H) 6.76 (dd, 1H) 7.06 (s, 1H) 7.28 (dd, 1H) T39

δ ppm 1.44 (s, 6H) 1.55 (s, 6H) 2.31 (s, 3H) 3.92 (s, 3H) 6.23 (s (br),1H) 6.88 (m, 1H) 7.06 (m, 1H) 7.15 (m, 1H) 7.17 (s, 1H) T40

δ ppm 1.45 (s, 6H) 1.55 (s, 6H) 2.30 (s, 3H) 4.07 (s, 3H) 6.94 (dd, 1H)7.25 (s, 1H) 7.85 (dd, 1H) 8.09 (dd, 1H) T41

δ ppm 1.50 (s, 12H) 2.38 (s, 3H) 5.2 (s, 1H) 7.4 (m, 2H) 7.5 (m, 1H);7.95 (m, 1H) T42

δ ppm 1.50 (s, 12H) 2.34 (s, 3H) 2.54 (s, 3H) 7.4 (d, 1H) 7.6 (d, 1H)7.7 (s, 1H) T43

δ ppm 1.50 (s, 12H) 2.35 (s, 3H) 7.5 (d, 1H) 7.65 (d, 1H) 7.9 (s, 1H)T44

δ ppm 1.50 (s, 12H) 2.35 (s, 3H) 2.55 (s, 3H) 7.26 (d, 1H) 7.3 (s, 1H)7.6 (d, 1H) T45

δ ppm 1.50 (s, 12H) 2.35 (s, 3H) 7.35 (dd, 1H) 7.52 (d, 1H) 7.9 (d, 1H)T46

δ ppm 1.55 (s, 12H) 2.37 (s, 3H) 7.09 (dd, 1H) 7.40 (d, 1H) 7.46 (d, 1H)T47

δ ppm 1.39 (t, 3H) 1.61 (5, 12H) 2.90 (q, 2H) 7.29 (m, 2H) 8.01 (m, 1H)T48

δ ppm 1.33 (t, 3H) 1.56 (s, 12H) 2.82 (q, 2H) 7.47 (m, 1H) 7.56 (m, 1H)7.64 (dd, 1H) T49

δ ppm 1.33 (t, 3H) 1.56 (s, 12H) 2.82 (q, 2H) 7.58 (m, 2H) 7.71 (m, 2H)T50

δ ppm 1.33 (t, 3H) 1.66 (s, 3H) 1.87-2.07 (m, 3H) 2.44 (m, 1H) 2.95 (q,2H) 4.77 (s, 1H), 7.42 (d, 2H) 7.75 (d, 2H) T51

δ ppm 1.56 (s, 12H) 2.40 (s, 3H) 7.55 (d, 2H) 7.78 (d, 2H) T52

δ ppm 1.56 (s, 12H) 2.42 (s, 3H) 7.40 (m, 1H) 7.43 (m, 1H) 7.89 (m, 1H)T53

δ ppm 1.28 (t, 3H) 1.49 (s, 12H) 2.79 (q, 2H) 7.29 (dd, 1H) 7.48 (d, 1H)7.82 (d, 1H) T54

δ ppm 1.34 (t, 3H) 1.56 (s, 12H) 2.85 (q, 2H) 7.40 (m, 1H) 7.42 (m, 1H)7.89 (m, 1H) T55

δ ppm 1.59 (s, 12H) 2.41 (s, 3H) 6.95 (d, 1H) 7.27 (d, 1H) T56

δ ppm 1.56 (s, 12H) 2.42 (s, 3H) 7.88 (d, 1H) 7.92 (dd, 1H) 8.66 (d, 1H)T57

δ ppm 1.34 (t, 3H) 1.55 (s, 12H) 2.56 (s, 3H) 2.84 (q, 2H) 7.42 (dd, 1H)7.48 (d, 1H) 7.52 (d, 1H) T58

δ ppm 1.55 (s, 12H) 2.42 (s, 3H) 2.55 (s, 3H) 7.41 (dd, 1H) 7.48 (d, 1H)7.51 (d, 1H) T59

δ ppm 1.54 (s, 12H) 2.35 (s, 3H) 5.26 (s, 2H) 6.90 (m, 2H) 7.27 (m, 2H)T60

δ ppm 1.56 (s, 12H) 2.41 (s, 3H) 6.57 (t, 1H) 7.20 (m, 2H) 7.83 (m, 2H)T61

δ ppm 1.34 (t, 3H) 1.55 (s, 12H) 2.56 (s, 3H) 2.84 (q, 2H) 7.32 (s, 1H)7.59 (d, 1H) 7.68 (d, 1H) T62

δ ppm 1.33 (t, 3H) 1.56 (s, 12H) 2.82 (q, 2H) 6.57 (t, 1H) 7.20 (m, 2H)7.85 (m, 2H) T63

δ ppm 1.35 (t, 3H) 1.56 (s, 12H) 2.82 (q, 2H) 7.80 (d, 1H) 7.93 (dd, 1H)8.66 (d, 1H) T64

δ ppm 1.34 (t, 3H) 1.54 (s, 12H) 2.41 (s, 3H) 2.86 (q, 2H) 7.08 (m, 1H)7.13 (m, 1H) T65

δ ppm 1.35 (t, 3H) 1.56 (s, 12H) 2.86 (q, 2H) 7.59 (d, 1H) 7.80 (d, 1H)T66

δ ppm 1.43 (s, 12H) 2.1 (s, 3H) 7.5 (d, 2H) 7.9 (d, 2H) T67

δ ppm 1.56 (s, 12H) 2.40 (s, 3H) 2.53 (s, 3H) 7.28 (m, 2H) 7.74 (m, 2H)T68

δ ppm 1.57 (s, 12H) 2.43 (s, 3H) 2.78 (s, 3H) 7.73 (m, 2H) 7.99 (m, 2H)T69

δ ppm 1.32 (t, 3H) 1.56 (s, 12H) 2.53 (s, 3H) 2.82 (q, 2H) 7.28 (m, 2H)7.75 (m, 2H) T70

δ ppm 1.56 (s, 12H) 2.43 (s, 3H) 6.58 (t, 1H) 7.16 (dd, 1H) 7.31 (d, 1H)7.95 (d, 1H) T71

δ ppm 1.55 (s, 12H) 2.19 (s, 3H) 7.55 (m, 2H) 8.21 (m, 2H) 8.60 (s, 1H)T72

δ ppm 1.48 (s, 6H) 1.63 (s, 6H) 2.57 (s, 3H) 7.48 (d, 2H) 7.90 (d, 2H)8.77 (s (br), 1H) T73

δ ppm 1.3 (t, 3H) 1.55 (s, 12H) 2.8 (q, 2H) 7.45 (m, 3H) 7.85 (m, 2H)T74

δ ppm 1.37 (t, 3H) 1.6 (s, 12H) 2.85 (q, 2H) 7.2 (m, 2H) 7.85 (m, 2H)T75

δ ppm 1.35 (t, 3H) 1.6 (s, 12H) 2.8 (q, 2H) 4.05 (s, 3H) 7.1 (m, 2H) 7.5(m, 1H) 8.0 (d, 1H) T76

δ ppm 1.35 (t, 3H) 1.6 (s, 12H) 2.85 (q, 2H) 7.7 (d, 2H) 7.95 (d, 2H)T77

δ ppm 1.3 (t, 3H) 1.55 (s, 12H) 2.8 (q, 2H) 7.40 (m, 1H) 7.45 (d, 1H)7.8 (s, 1H) 9.0 (s br, 1H) T78

δ ppm 1.3 (t, 3H) 1.55 (s, 12H) 2.8 (q, 2H) 7.5 (m, 2H) 7.90 (m, 4H) 8.3(s, 1H) 9.1 (s br, 1H) T79

δ ppm 1.35 (t, 3H) 1.6 (s, 12H) 2.85 (q, 2H) 7.0 (m, 2H) 8.0 (m, 1H) T80

δ ppm 0.95 (t, 3H) 1.52 (s, 3H) 1.53 (s, 3H) 1.58 (s, 3H) 1.74 (m, 1H)1.97 (m, 1H) 2.41 (s, 3H) 7.41 (d, 2H) 7.73 (d, 2H) T81

δ ppm 1.65 (s, 12 H) 2.26 (s, 3H) 7.42 (d, 2H) 7.76 (d, 2H)

Example 8 Preparation of 2,2-dimethylpropionic acid4-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-ylester (Compound P2 in Table P1)

To a solution of4-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione(49 mg, 0.125 mmol) in dichloromethane (2 ml) is added triethylamine (87μl, 0.625 mmol), followed by pivaloyl chloride (78 μl, 0.625 mmol), andthe reaction mixture is stirred at room temperature for 17 hours. Thereaction mixture is purified by flash chromatography on silica gel togive 2,2-dimethylpropionic acid4-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-ylester.

Additional compounds in Table P1 below are prepared by similar methodsusing appropriate starting materials.

TABLE P1 Compound ¹H nmr (CDCl₃ unless stated) or Number Structure otherphysical data P1

δ ppm 1.00 (s, 9H) 1.29 (t, 3H) 1.48 (s, 6) 1.51 (s, 6H) 2.63 (q, 2H)7.37 (m, 2H) 7.80 (m, 2H) P2

δ ppm 0.98 (s, 9H) 1.29 (t, 3H) 1.52 (s, 6H) 1.55 (s, 6H) 2.61 (q, 2H)7.36 (m 2H) 7.81 (d, 2H) P3

δ ppm 1.53 (s, 6H) 1.57 (s, 6H) 1.91 (s 3H) 2.28 (s, 3H) 7.86 (dd, 1H)8.04 (d, 1H) 8.62 (d, 1H) P4

δ ppm 0.73 (m, 4H) 1.49 (m, 1H) 1.52 (s, 6H) 1.57 (s, 6H) 2.27 (s, 3H)7.86 (dd, 1H) 8.05 (d, 1H) 8.61 (d, 1H) P5

δ ppm 0.99 (s, 9H) 1.53 (s, 6H) 1.55 (s, 6H) 2.28 (s, 3H) 7.85 (dd, 1H)8.01 (d, 1H) 8.60 (d, 1H) P6

δ ppm 1.53 (s, 6H) 1.56 (s, 6H) 1.93 (s, 3H) 2.28 (s, 3H) 2.53 (s, 3H)7.36 (dd, 1H) 7.43 (d, 1H) 7.54 (d, 1H) P7

δ ppm 0.76 (m, 4H) 1.52-1.57 (m, 13H) 2.27 (s, 3H) 2.54 (s, 3H) 7.36(dd, 1H) 7.42 (d, 1H) 7.54 (d, 1H) P8

δ ppm 1.02 (s, 9H) 1.53 (s, 6H) 1.55 (s, 6H) 2.28 (s, 3H) 2.53 (s, 3H)7.35 (dd, 1H) 7.41 (d, 1H) 7.56 (d, 1H) P9

δ ppm 1.52 (s, 6H) 1.55 (s 6H) 2.01 (s, 3H) 2.32 (s, 3H) 7.40 (d 2H)7.85 (d 2H) P10

δ ppm 0.99 (s, 9H) 1.53 (s, 6H) 1.55 (s, 6H) 2.29 (s, 3H) 6.55 (t, 1H)7.09 (dd, 1H) 7.24 (d, 1H) 8.22 (d, 1H) P11

δ ppm 1.29 (t, 3H) 1.57 (s, 6H) 1.66 (s, 6H) 2.64 (q, 2H) 7.24 (m, 2H)7.31 (m, 2H) 7.48 (m, 1H) 7.54 (m, 2H) 7.87 (m, 2H) P12

δ ppm 1.32 (t, 3H) 1.51 (s, 6H) 1.67 (s, 6H) 2.49 (s, 3H) 2.64 (q, 2H)7.39 (m, 2H) 7.84 (d, 2H) P13

δ ppm 1.0 (s, 9H) 1.5 (d, 12H) 2.3 (s, 3H) 7.19 (d, 2H) 8.17 (t, 1H) P14

δ ppm 1.0 (s, 9H) 1.59 (d, 12H) 2.30 (s, 3H) 7.2 (d, 1H) 7.4 (d, 1H) 8.2(s, 1H) P15

δ ppm 1.29 (t, 3H) 1.57 (s, 6H) 1.66 (s, 6H) 2.64 (q, 2H) 7.24 (m, 2H)7.31 (m, 2H) 7.48 (m, 1H) 7.54 (m, 2H) 7.87 (m, 2H) P16

δ ppm 1.32 (t, 3H) 1.51 (s, 6H) 1.67 (s, 6H) 2.49 (s, 3H) 2.64 (q, 2H)7.39 (m, 2H) 7.84 (m, 2H) P17

δ ppm 1.29 (t, 3H) 1.53 (s, 6H) 1.66 (s, 6H) 2.64 (q, 2H) 6.80 (m, 2H)7.20 (m, 3H) 7.35 (m, 2H) 7.82 (d, 2H) P18

δ ppm 1.10 (t, 3H) 1.50 (s, 6H) 1.73 (s, 6H) 2.39 (s (br), 2H) 2.64 (q,2H) 7.21 (m, 2H) 7.34 (d, 2H) 7.46 (m, 3H) 7.67 (m, 2H)

Table 1:

This table covers 126 compounds of the structural type T-1:

wherein Y is O, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined below:

Compound Number R⁷ R⁸ R¹⁴ 1.001 CH₃ H H 1.002 CH₃ H CH₃ 1.003 CH₃ CH₃ H1.004 CH₃ CH₃ CH₃ 1.005 CH₃ CH₃CH₂ CH₃ 1.006 CH₃CH₂ H H 1.007 CH₃CH₂ HCH₃ 1.008 CH₃CH₂ CH₃ H 1.009 CH₃CH₂ CH₃ CH₃ 1.010 CH₃CH₂ H CH₃CH₂ 1.011CH₃CH₂ CH₃ CH₃CH₂ 1.012 CH₃CH₂ CH₃CH₂ H 1.013 CH₃CH₂ CH₃CH₂ CH₃ 1.014CH₃CH₂ CH₃CH₂ CH₃CH₂ 1.015 CH₃ phenyl H 1.016 CH₃ 2-fluorophenyl H 1.017CH₃ 3-fluorophenyl H 1.018 CH₃ 4-fluorophenyl H 1.019 CH₃ 2-chlorophenylH 1.020 CH₃ 3-chlorophenyl H 1.021 CH₃ 4-chlorophenyl H 1.022 CH₃2-bromophenyl H 1.023 CH₃ 3-bromophenyl H 1.024 CH₃ 4-bromophenyl H1.025 CH₃ 2-methylphenyl H 1.026 CH₃ 3-methylphenyl H 1.027 CH₃4-methylphenyl H 1.028 CH₃ 2-cyanophenyl H 1.029 CH₃ 3-cyanophenyl H1.030 CH₃ 4-cyanophenyl H 1.031 CH₃ 2-methoxyphenyl H 1.032 CH₃3-methoxyphenyl H 1.033 CH₃ 4-methoxyphenyl H 1.034 CH₃2-trifluoromethylphenyl H 1.035 CH₃ 3-trifluoromethylphenyl H 1.036 CH₃4-trifluoromethylphenyl H 1.037 CH₃ 4-trifluoromethoxyphenyl H 1.038 CH₃4-difluoromethoxyphenyl H 1.039 CH₃ 4-methylthiophenyl H 1.040 CH₃4-methylsulfinylphenyl H 1.041 CH₃ 4-methylsulfonylphenyl H 1.042 CH₃4-trifluoromethylthiophenyl H 1.043 CH₃ 4-trifluoromethylsulfinylphenylH 1.044 CH₃ 4-trifluoromethylsulfonylphenyl H 1.045 CH₃2,3-difluorophenyl H 1.046 CH₃ 2,4-difluorophenyl H 1.047 CH₃2,5-difluorophenyl H 1.048 CH₃ 2,6-difluorophenyl H 1.049 CH₃3,4-difluorophenyl H 1.050 CH₃ 3,5-difluorophenyl H 1.051 CH₃2,3-dichlorophenyl H 1.052 CH₃ 2,4-dichlorophenyl H 1.053 CH₃2,5-dichlorophenyl H 1.054 CH₃ 2,6-dichlorophenyl H 1.055 CH₃3,4-dichlorophenyl H 1.056 CH₃ 3,5-dichlorophenyl H 1.057 CH₃4-chloro-2-fluorophenyl H 1.058 CH₃ 4-chloro-3-fluorophenyl H 1.059 CH₃4-chloro-2-methylphenyl H 1.060 CH₃ 4-chloro-3-methylphenyl H 1.061 CH₃2-fluoro-4-trifluoromethylphenyl H 1.062 CH₃3-fluoro-4-trifluoromethylphenyl H 1.063 CH₃ 2-chloropyridin-5-yl H1.064 CH₃ 3-chloropyridinyl-5-yl H 1.065 CH₃ 2-methylpyridin-5-yl H1.066 CH₃ 3-methylpyridinyl-5-yl H 1.067 CH₃2-trifluoromethylpyridin-5-yl H 1.068 CH₃ 3-trifluoromethylpyridin-5-ylH 1.069 CH₃ 2,6-dichloropyridin-3-yl H 1.070 CH₃ 4-chloropyrazol-1-yl H1.071 CH₃CH₂ phenyl H 1.072 CH₃CH₂ 2-fluorophenyl H 1.073 CH₃CH₂3-fluorophenyl H 1.074 CH₃CH₂ 4-fluorophenyl H 1.075 CH₃CH₂2-chlorophenyl H 1.076 CH₃CH₂ 3-chlorophenyl H 1.077 CH₃CH₂4-chlorophenyl H 1.078 CH₃CH₂ 2-bromophenyl H 1.079 CH₃CH₂ 3-bromophenylH 1.080 CH₃CH₂ 4-bromophenyl H 1.081 CH₃CH₂ 2-methylphenyl H 1.082CH₃CH₂ 3-methylphenyl H 1.083 CH₃CH₂ 4-methylphenyl H 1.084 CH₃CH₂2-cyanophenyl H 1.085 CH₃CH₂ 3-cyanophenyl H 1.086 CH₃CH₂ 4-cyanophenylH 1.087 CH₃CH₂ 2-methoxyphenyl H 1.088 CH₃CH₂ 3-methoxyphenyl H 1.089CH₃CH₂ 4-methoxyphenyl H 1.090 CH₃CH₂ 2-trifluoromethylphenyl H 1.091CH₃CH₂ 3-trifluoromethylphenyl H 1.092 CH₃CH₂ 4-trifluoromethylphenyl H1.093 CH₃CH₂ 4-trifluoromethoxyphenyl H 1.094 CH₃CH₂4-difluoromethoxyphenyl H 1.095 CH₃CH₂ 4-methylthiophenyl H 1.096 CH₃CH₂4-methylsulfinylphenyl H 1.097 CH₃CH₂ 4-methylsulfonylphenyl H 1.098CH₃CH₂ 4-trifluoromethylthiophenyl H 1.099 CH₃CH₂4-trifluoromethylsulfinylphenyl H 1.100 CH₃CH₂4-trifluoromethylsulfonylphenyl H 1.101 CH₃CH₂ 2,3-difluorophenyl H1.102 CH₃CH₂ 2,4-difluorophenyl H 1.103 CH₃CH₂ 2,5-difluorophenyl H1.104 CH₃CH₂ 2,6-difluorophenyl H 1.105 CH₃CH₂ 3,4-difluorophenyl H1.106 CH₃CH₂ 3,5-difluorophenyl H 1.107 CH₃CH₂ 2,3-dichlorophenyl H1.108 CH₃CH₂ 2,4-dichlorophenyl H 1.109 CH₃CH₂ 2,5-dichlorophenyl H1.110 CH₃CH₂ 2,6-dichlorophenyl H 1.111 CH₃CH₂ 3,4-dichlorophenyl H1.112 CH₃CH₂ 3,5-dichlorophenyl H 1.113 CH₃CH₂ 4-chloro-2-fluorophenyl H1.114 CH₃CH₂ 4-chloro-3-fluorophenyl H 1.115 CH₃CH₂4-chloro-2-methylphenyl H 1.116 CH₃CH₂ 4-chloro-3-methylphenyl H 1.117CH₃CH₂ 2-fluoro-4-trifluoromethylphenyl H 1.118 CH₃CH₂3-fluoro-4-trifluoromethylphenyl H 1.119 CH₃CH₂ 2-chloropyridin-5-yl H1.120 CH₃CH₂ 3-chloropyridinyl-5-yl H 1.121 CH₃CH₂ 2-methylpyridin-5-ylH 1.122 CH₃CH₂ 3-methylpyridinyl-5-yl H 1.123 CH₃CH₂2-trifluoromethylpyridin-5-yl H 1.124 CH₃CH₂3-trifluoromethylpyridin-5-yl H 1.125 CH₃CH₂ 2,6-dichloropyridin-3-yl H1.126 CH₃CH₂ 4-chloropyrazol-1-yl H

Table 2:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 3:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 4:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 5:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 6:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1.

Table 7:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 8:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 9:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 10:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 11:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 12:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 13:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 14:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 15:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 16:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 17:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 18:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 19:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 20:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 21:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 22:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 23:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 24:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 25:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 26:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 27:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 28:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 29:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 30:

This table covers 126 compounds of the structural type T-1, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 31:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹, R², R³ and

R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴ are as defined inTable 1.

Table 32:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is methyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 33:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 34:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 35:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 36:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1.

Table 37:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 38:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 39:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 40:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 41:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 42:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 43:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 44:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 45:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 46:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 47:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 48:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 49:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 50:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 51:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 52:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 53:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 54:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 55:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 56:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 57:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 58:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 59:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 60:

This table covers 126 compounds of the structural type T-1, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 61:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1.

Table 62:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 63:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R² are methyl, R³ and R⁴ are, hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 64:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 65:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 66:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ areas defined in Table 1.

Table 67:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 68:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 69:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 70:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 71:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 72:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 73:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 74:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 75:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 76:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 77:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 78:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 79:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 80:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 81:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 82:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 83:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 84:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 85:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 86:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 87:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 88:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 89:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 90:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 91:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1.

Table 92:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, W is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 93:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 94:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 95:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 96:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1.

Table 97:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 98:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 99:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ is ethyl, R² and R3 are hydrogen, R⁴ is methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 100:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ is ethyl, R² and R3 are methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 101:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 102:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 103:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 104:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 105:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table

Table 106:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 107:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1:

Table 108:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 109:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 110:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 111:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 112:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 113:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 114:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 115:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 116:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 117:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 118:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 119:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 120:

This table covers 126 compounds of the structural type T-1, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 121:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 122:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 123:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ areas defined in Table 1.

Table 124:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 125:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 126:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 127:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 128:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 129:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 130:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 131:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 132:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 133:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 134:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 135:

This table covers 126 compounds of the structural type T-1 wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 136:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 137:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 138:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 139:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 140:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 141:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 142:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 143:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 144:

This table covers 126 compounds of the structural type T-1, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 145:

This table covers 126 compounds of the structural type T-2:

wherein Y is O, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 146:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 147:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 148:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 149:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 150:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1.

Table 151:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 152:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 153:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 154:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 155:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 156:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 157:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 158:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 159:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 160:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 161:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 162:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 163:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 164:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 165:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 166:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 167:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 168:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring,

R³ is hydrogen, R⁴ is methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1.

Table 169:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 170:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 171:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 172:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 173:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 174:

This table covers 126 compounds of the structural type T-2, wherein Y isO, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 175:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴ areas defined in Table 1.

Table 176:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 177:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R² are methyl, R3 and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 178:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 179:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 180:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1.

Table 181:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 182:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 183:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 184:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 185:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 186:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 187:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 188:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 189:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 190:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 191:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1:

Table 192:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 193:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 194:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 195:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 196:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 197:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 198:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 199:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 200:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 201:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 202:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 203:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 204:

This table covers 126 compounds of the structural type T-2, wherein Y isS, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 205:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1

Table 206:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 207:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 208:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 209:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 210:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ areas defined in Table 1.

Table 211:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 212:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 213:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 214:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 215:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 216:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 217:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 218:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 219:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 220:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 221:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 222:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 223:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 224:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 225:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 226:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 227:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 228:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 229:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 230:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 231:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 232:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 233:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 234:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 235:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1.

Table 236:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 237:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 238:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 239:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 240:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1.

Table 241:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 242:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 243:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 244:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 245:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 246:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 247:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 248:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 249:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 250:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 251:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 252:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 253:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 254:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 255:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 256:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 257:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 258:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 259:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 260:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 261:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 262:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 263:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 264:

This table covers 126 compounds of the structural type T-2, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 265:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 266:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 267:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ areas defined in Table 1.

Table 268:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 269:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 270:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 271:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸ andR¹⁴ are as defined in Table 1.

Table 272:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 273:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 274:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷,R⁸ and R¹⁴ are as defined in Table 1.

Table 275:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R² are ethyl, R³ is methyl, R⁴ is hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 276:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸and R¹⁴ are as defined in Table 1.

Table 277:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 278:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 279:

This table covers 126 compounds of the structural type T-2 wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 280:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 281:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 282:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 283:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 284:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 285:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 286:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 287:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 288:

This table covers 126 compounds of the structural type T-2, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷, R⁸ and R¹⁴ are as defined in Table 1.

Table 289:

This table covers 118 compounds of structural type T-3:

wherein Y is O, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined below:

Compound Number R⁷ R⁸ 289.001 CH₃ H 289.002 CH₃ CH₃ 289.003 CH₃ CH₃CH₂289.004 CH₃CH₂ H 289.005 CH₃CH₂ CH₃ 289.006 CH₃CH₂ CH₃CH₂ 289.007 CH₃phenyl 289.008 CH₃ 2-fluorophenyl 289.009 CH₃ 3-fluorophenyl 289.010 CH₃4-fluorophenyl 289.011 CH₃ 2-chlorophenyl 289.012 CH₃ 3-chlorophenyl289.013 CH₃ 4-chlorophenyl 289.014 CH₃ 2-bromophenyl 289.015 CH₃3-bromophenyl 289.016 CH₃ 4-bromophenyl 289.017 CH₃ 2-methylphenyl289.018 CH₃ 3-methylphenyl 289.019 CH₃ 4-methylphenyl 289.020 CH₃2-cyanophenyl 289.021 CH₃ 3-cyanophenyl 289.022 CH₃ 4-cyanophenyl289.023 CH₃ 2-methoxyphenyl 289.024 CH₃ 3-methoxyphenyl 289.025 CH₃4-methoxyphenyl 289.026 CH₃ 2-trifluoromethylphenyl 289.027 CH₃3-trifluoromethylphenyl 289.028 CH₃ 4-trifluoromethylphenyl 289.029 CH₃4-trifluoromethoxyphenyl 289.030 CH₃ 4-difluoromethoxyphenyl 289.031 CH₃4-methylthiophenyl 289.032 CH₃ 4-methylsulfinylphenyl 289.033 CH₃4-methylsulfonylphenyl 289.034 CH₃ 4-trifluoromethylthiophenyl 289.035CH₃ 4-trifluoromethylsulfinylphenyl 289.036 CH₃4-trifluoromethylsulfonylphenyl 289.037 CH₃ 2,3-difluorophenyl 289.038CH₃ 2,4-difluorophenyl 289.039 CH₃ 2,5-difluorophenyl 289.040 CH₃2,6-difluorophenyl 289.041 CH₃ 3,4-difluorophenyl 289.042 CH₃3,5-difluorophenyl 289.043 CH₃ 2,3-dichlorophenyl 289.044 CH₃2,4-dichlorophenyl 289.045 CH₃ 2,5-dichlorophenyl 289.046 CH₃2,6-dichlorophenyl 289.047 CH₃ 3,4-dichlorophenyl 289.048 CH₃3,5-dichlorophenyl 289.049 CH₃ 4-chloro-2-fluorophenyl 289.050 CH₃4-chloro-3-fluorophenyl 289.051 CH₃ 4-chloro-2-methylphenyl 289.052 CH₃4-chloro-3-methylphenyl 289.053 CH₃ 2-fluoro-4-trifluoromethylphenyl289.054 CH₃ 3-fluoro-4-trifluoromethylphenyl 289.055 CH₃2-chloropyridin-5-yl 289.056 CH₃ 3-chloropyridinyl-5-yl 289.057 CH₃2-methylpyridin-5-yl 289.058 CH₃ 3-methylpyridinyl-5-yl 289.059 CH₃2-trifluoromethylpyridin-5-yl 289.060 CH₃ 3-trifluoromethylpyridin-5-yl289.061 CH₃ 2,6-dichloropyridin-3-yl 289.062 CH₃ 4-chloropyrazol-1-yl289.063 CH₃CH₂ phenyl 289.064 CH₃CH₂ 2-fluorophenyl 289.065 CH₃CH₂3-fluorophenyl 289.066 CH₃CH₂ 4-fluorophenyl 289.067 CH₃CH₂2-chlorophenyl 289.068 CH₃CH₂ 3-chlorophenyl 289.069 CH₃CH₂4-chlorophenyl 289.070 CH₃CH₂ 2-bromophenyl 289.071 CH₃CH₂ 3-bromophenyl289.072 CH₃CH₂ 4-bromophenyl 289.073 CH₃CH₂ 2-methylphenyl 289.074CH₃CH₂ 3-methylphenyl 289.075 CH₃CH₂ 4-methylphenyl 289.076 CH₃CH₂2-cyanophenyl 289.077 CH₃CH₂ 3-cyanophenyl 289.078 CH₃CH₂ 4-cyanophenyl289.079 CH₃CH₂ 2-methoxyphenyl 289.080 CH₃CH₂ 3-methoxyphenyl 289.081CH₃CH₂ 4-methoxyphenyl 289.082 CH₃CH₂ 2-trifluoromethylphenyl 289.083CH₃CH₂ 3-trifluoromethylphenyl 289.084 CH₃CH₂ 4-trifluoromethylphenyl289.085 CH₃CH₂ 4-trifluoromethoxyphenyl 289.086 CH₃CH₂4-difluoromethoxyphenyl 289.087 CH₃CH₂ 4-methylthiophenyl 289.088 CH₃CH₂4-methylsulfinylphenyl 289.089 CH₃CH₂ 4-methylsulfonylphenyl 289.090CH₃CH₂ 4-trifluoromethylthiophenyl 289.091 CH₃CH₂4-trifluoromethylsulfinylphenyl 289.092 CH₃CH₂4-trifluoromethylsulfonylphenyl 289.093 CH₃CH₂ 2,3-difluorophenyl289.094 CH₃CH₂ 2,4-difluorophenyl 289.095 CH₃CH₂ 2,5-difluorophenyl289.096 CH₃CH₂ 2,6-difluorophenyl 289.097 CH₃CH₂ 3,4-difluorophenyl289.098 CH₃CH₂ 3,5-difluorophenyl 289.099 CH₃CH₂ 2,3-dichlorophenyl289.100 CH₃CH₂ 2,4-dichlorophenyl 289.101 CH₃CH₂ 2,5-dichlorophenyl289.102 CH₃CH₂ 2,6-dichlorophenyl 289.103 CH₃CH₂ 3,4-dichlorophenyl289.104 CH₃CH₂ 3,5-dichlorophenyl 289.105 CH₃CH₂ 4-chloro-2-fluorophenyl289.106 CH₃CH₂ 4-chloro-3-fluorophenyl 289.107 CH₃CH₂4-chloro-2-methylphenyl 289.108 CH₃CH₂ 4-chloro-3-methylphenyl 289.109CH₃CH₂ 2-fluoro-4-trifluoromethylphenyl 289.110 CH₃CH₂3-fluoro-4-trifluoromethylphenyl 289.111 CH₃CH₂ 2-chloropyridin-5-yl289.112 CH₃CH₂ 3-chloropyridinyl-5-yl 289.113 CH₃CH₂2-methylpyridin-5-yl 289.114 CH₃CH₂ 3-methylpyridinyl-5-yl 289.115CH₃CH₂ 2-trifluoromethylpyridin-5-yl 289.116 CH₃CH₂3-trifluoromethylpyridin-5-yl 289.117 CH₃CH₂ 2,6-dichloropyridin-3-yl289.118 CH₃CH₂ 4-chloropyrazol-1-yl

Table 290:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 291:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 292:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 293

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 294:

This table covers 118 compounds of structural type T-3, wherein Y is O,Fe, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 295:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 88:

Table 296:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 297:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 298:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 299:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 300:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 301:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 302:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 303:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 304:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 305:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 306:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 307:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 308:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 309:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 310:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 311:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 312:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 313:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 314:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 315:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 316:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 317:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 318:

This table covers 118 compounds of structural type T-3, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 319:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 320:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 321:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R² are methyl, R3 and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 322:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 323:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 324:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 325:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 326:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 327:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is ethyl, R² and R3 are hydrogen, R⁴ is methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 328:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 329:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 330:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 331:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 332:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 333:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 334:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 335:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 336:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 337:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 338:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 339:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 340:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 341:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 342:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 343:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 344:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 345:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 346:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 347:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 348:

This table covers 118 compounds of structural type T-3, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 349:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 350:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 351:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 352:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 353:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 354:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 355:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 356:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 357:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), Fe is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 358:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 359:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 360:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 361:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 362:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 363:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 364:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 365:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 366:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 367:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 368:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 369:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 370:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 371:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 372:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), Fe and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 373:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 374:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 375:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 376:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 377:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 378:

This table covers 118 compounds of structural type T-3, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 379:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 380:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 381:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R² are methyl, R3 and R⁴ are hydrogen, G is hydrogen andR⁷ and R⁸ are as defined in Table 289.

Table 382:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷ and R⁸ are as defined in Table 289.

Table 383:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 384:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, Fe, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 385:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 386:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 387:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is ethyl, R² and R3 are hydrogen, R⁴ is methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 388:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 389:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 390:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 391:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 392:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 393:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 394:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 395:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 396:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 397:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 398:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 399:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 400:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 401:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 402:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 403:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 404:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 405:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 406:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 407:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 408:

This table covers 118 compounds of structural type T-3, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 409:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 410:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 411:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 412:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 413:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 414:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 415:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 416:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 417:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 418:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R² are ethyl, R^(a) and R⁴ are hydrogen, G is hydrogen andR⁷ and R⁸ are as defined in Table 289.

Table 419:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 420:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 421:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 422:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, Fe and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 423:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 424:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 425:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 426:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 427:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 428:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 429:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 430:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 431:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 432:

This table covers 118 compounds of structural type T-3, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 433:

This table covers 118 compounds of structural type T-4:

wherein Y is O, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 434:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 435:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 436:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 437

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 438:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 439:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 88:

Table 440:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 441:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 442:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 443:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 444:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 445:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 446:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 447:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 448:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 449:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 450:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 451:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 452:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 453:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 454:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 455:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 456:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 457:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 458:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 459:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 460:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 461:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 462:

This table covers 118 compounds of structural type T-4, wherein Y is O,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 463:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 464:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 465:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 466:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 467:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 468:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 469:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 470:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 471:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 472:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 473:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 474:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 475:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 476:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 477:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 478:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 479:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 480:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 481:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 482:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 483:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 484:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 485:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 486:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 487:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 488:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 489:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 490:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 491:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 492:

This table covers 118 compounds of structural type T-4, wherein Y is S,R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 493:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 494:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 495:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 496:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), Fe and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 497:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 498:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 499:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 500:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 501:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is ethyl, R² and R³ are hydrogen, R⁴ is methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 502:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 503:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 504:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 505:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 506:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 507:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 508:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 509:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 510:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 511:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 512:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 513:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 514:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 515:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 516:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 517:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 518:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 519:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 520:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 521:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 522:

This table covers 118 compounds of structural type T-4, wherein Y isS(O), Fe and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 523:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 524:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is methyl R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 525:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen andR⁷ and R⁸ are as defined in Table 289.

Table 526:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R³ are methyl, R² and R⁴ are hydrogen, G is hydrogen andR⁷ and R⁸ are as defined in Table 289.

Table 527:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 528:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 529:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 530:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 531:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is ethyl, R² and R3 are hydrogen, R⁴ is methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 532:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 533:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 534:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 535:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 536:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 537:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 538:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 539:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 540:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 541:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 542:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 543:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 544:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 545:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 546:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 547:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 548:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, Gis hydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 549:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopropane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 550:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclobutane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 551:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclopentane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 552:

This table covers 118 compounds of structural type T-4, wherein Y isS(O)₂, R¹ and R², together with the carbon to which they are attached,are joined to form a cyclohexane ring, R³ and R⁴ are methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 553:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R² are methyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 554:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹, R², and R³ are methyl, R⁴ is hydrogen, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 555:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are asdefined in Table 289.

Table 556:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ is ethyl, R² is methyl, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 557:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ is ethyl, R² and R³ are methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 558:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ is ethyl, R² is hydrogen, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 559:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ is ethyl, R², R³ and R⁴ are methyl, G is hydrogen and R⁷ and R⁸are as defined in Table 289.

Table 560:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 561:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 562:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R² are ethyl, R³ and R⁴ are hydrogen, G is hydrogen and R⁷and R⁸ are as defined in Table 289.

Table 563:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R³ are ethyl, R² is methyl, R⁴ is hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 564:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R³ are ethyl, R² and R⁴ are methyl, G is hydrogen and R⁷ andR⁸ are as defined in Table 289.

Table 565:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 566:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 567:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are hydrogen, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 568:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are hydrogen, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 569:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 570:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 571:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 572:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ is hydrogen, R⁴ is methyl, G ishydrogen and R⁷ and R⁸ are as defined in Table 289.

Table 573:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopropane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 574:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclobutane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 575:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclopentane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 576:

This table covers 118 compounds of structural type T-4, wherein Y isC═O, R¹ and R², together with the carbon to which they are attached, arejoined to form a cyclohexane ring, R³ and R⁴ are methyl, G is hydrogenand R⁷ and R⁸ are as defined in Table 289.

Table 577:

This table covers 122 compounds of the structural type T-5

wherein Y is O, R² and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1:

Table 578:

This table covers 122 compounds of the structural type T-5, wherein Y isO, R² is hydrogen, R⁴ is methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1:

Table 579:

This table covers 122 compounds of the structural type T-5, wherein Y isO, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are as definedin Table 1.

Table 580:

This table covers 122 compounds of the structural type T-5, wherein Y isO, R² is hydrogen, R⁴ is ethyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1:

Table 581:

This table covers 122 compounds of the structural type T-6

wherein Y is O, R² and R⁴ are hydrogen, G is hydrogen and R⁷, R⁸ and R¹⁴are as defined in Table 1:

Table 582:

This table covers 122 compounds of the structural type T-6, wherein Y isO, R² is hydrogen, R⁴ is methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1:

Table 583:

This table covers 122 compounds of the structural type T-6, wherein Y isO, R² and R⁴ are methyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are as definedin Table 1.

Table 584:

This table covers 122 compounds of the structural type T-6, wherein Y isO, R² is hydrogen, R⁴ is ethyl, G is hydrogen and R⁷, R⁸ and R¹⁴ are asdefined in Table 1:

Table 585:

This table covers 118 compounds of structural type T-7:

wherein Y is O, R² and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 586:

This table covers 118 compounds of structural type T-7, wherein Y is O,R² is hydrogen, R⁴ is methyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 587:

This table covers 118 compounds of structural type T-7, wherein Y is O,R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are as defined inTable 289.

Table 588:

This table covers 118 compounds of structural type T-7, wherein Y is O,R² is hydrogen, R⁴ is ethyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 589:

This table covers 118 compounds of structural type T-8:

wherein Y is O, R² and R⁴ are hydrogen, G is hydrogen and R⁷ and R⁸ areas defined in Table 289.

Table 590:

This table covers 118 compounds of structural type T-8, wherein Y is O,R² is hydrogen, R⁴ is methyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

Table 591:

This table covers 118 compounds of structural type T-8, wherein Y is O,R² and R⁴ are methyl, G is hydrogen and R⁷ and R⁸ are as defined inTable 289.

Table 592:

This table covers 118 compounds of structural type T-8, wherein Y is O,R² is hydrogen, R⁴ is ethyl, G is hydrogen and R⁷ and R⁸ are as definedin Table 289.

BIOLOGICAL EXAMPLES Example A

Seeds of a variety of test species were sown in standard soil in pots.After cultivation for one day (pre-emergence) or after 10 dayscultivation (post-emergence) under controlled conditions in aglasshouse, the plants were sprayed with an aqueous spray solutionderived from the formulation of the technical active ingredient in 0.6ml acetone and 45 ml formulation solution containing 10.6% Emulsogen EL(Registry number 61791-12-6), 42.2% N-methylpyrrolidone, 42.2%dipropylene glycol monomethyl ether (Registry number 34590-94-8) and0.2% X-77 (Registry number 11097-66-8). The test plants were then grownin a greenhouse under optimum conditions until, 14 or 15 days later forpost-emergence and 20 days for pre-emergence, the test was evaluated(100=total damage to plant; 0=no damage to plant).

Test Plants:

Alopecurus myosuroides (ALOMY), Avena fatua (AVEFA), Lolium perenne(LOLPE), Setaria faberi (SETFA), Digitaria sanguinalis (DIGSA),Echinochloa crus-galli (ECHCG)

Pre-Emergence Activity Compound Rate Number g/ha ALOMY AVEFA LOLPE SETFADIGSA ECHCG T6 250 50 20 80 60 70 50 T11 250 100 100 100 100 100 100 T12250 30 0 0 0 20 40 T13 250 100 50 100 100 100 100 T16 250 90 50 100 0100 60

Post-Emergence Activity Compound Rate Number g/ha ALOMY AVEFA LOLPESETFA DIGSA ECHCG T6 125 70 60 30 70 70 70 T11 125 90 80 60 100 100 100T12 125 80 70 70 80 90 100 T13 125 90 80 70 100 100 100 T16 125 70 70 6090 90 100

Example B

Seeds of a variety of test species were sown in standard soil in pots.After cultivation for one day (pre-emergence) or after 8 dayscultivation (post-emergence) under controlled conditions in a glasshouse(at 24/16° C., day/night; 14 hours light; 65% humidity), the plants weresprayed with an aqueous spray solution derived from the formulation ofthe technical active ingredient in acetone/water (50:50) solutioncontaining 0.5% Tween 20 (polyoxyethelyene sorbitan monolaurate, CAS RN9005-64-5).

The test plants were then grown in a glasshouse under controlledconditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65%humidity) and watered twice daily. After 13 days for pre andpost-emergence, the test was evaluated (100=total damage to plant; 0=nodamage to plant).

Test Plants:

Alopecurus myosuroides (ALOMY), Avena fatua (AVEFA), Setaria faberi(SETFA), Echinochloa crus-galli (ECHCG), Solanum nigrum (SOLNI) andAmaranthus retoflexus (AMARE)

Pre-Emergence Activity Compound Rate Number g/ha AVEFA SOLNI AMARE SETFAALOMY ECHCG T2 1000 0 60 50 0 0 0 T8 1000 20 0 0 0 30 0 T10 1000 20 0 00 30 0 T14 1000 0 0 0 0 40 0 T20 1000 0 70 80 0 30 0 P2 1000 30 0 80 8060 50 Compound Rate Number g/ha AMARE SEFTA ALOMY ECHGG AVEFA T21 250 0100 60 100 0 T9 250 0 40 0 20 0 T14 250 0 50 0 0 0 T22 250 0 100 70 9020 T42 250 40 0 0 40 0 T43 250 0 0 0 0 0 T44 250 0 0 0 30 0 T47 250 2090 70 70 90 T48 250 0 70 30 50 60 T49 250 0 80 60 60 20 T50 250 0 100 90100 90 T51 250 0 100 40 60 80 T52 250 0 100 60 80 0 T53 250 0 90 30 60 0T54 250 20 100 100 100 90 T55 250 0 50 0 20 0 T56 250 0 20 0 10 0 T57250 0 90 20 50 30 T58 250 20 100 0 50 0 T59 250 0 0 0 0 0 T60 250 0 7040 20 0 T61 250 0 100 80 100 0 T62 250 0 100 90 60 0 T63 250 0 20 20 3020 T64 250 0 100 0 70 0 T68 250 0 20 0 20 0 T69 250 0 20 0 20 0 T70 2500 70 30 70 0 T71 250 0 50 20 60 0 P3 250 0 20 20 30 0 P4 250 0 20 0 10 0P5 250 0 0 0 0 0 P6 250 0 100 90 70 80 P7 250 0 100 70 80 0 P9 250 0 4020 50 0

Post-Emergence Activity Compound Rate Number g/ha AVEFA SOLNI AMARESETFA ALOMY ECHCG T1 1000 80 0 0 90 90 90 T2 1000 0 40 0 0 0 0 T6 100090 0 0 100 90 90 T8 1000 0 20 0 80 40 70 T10 1000 0 20 0 80 40 70 T151000 0 0 0 0 40 70 T20 1000 0 0 0 10 0 0 P2 1000 90 0 0 100 90 100Compound Rate Number g/ha AMARE SEFTA ALOMY ECHGG AVEFA T5 250 0 50 4070 0 T9 250 0 80 90 90 40 T14 250 0 90 40 70 0 T21 250 0 100 100 100 90T22 250 0 100 100 100 90 T25 250 0 20 0 20 0 T27 250 30 50 20 30 0 T42250 0 0 0 20 0 T43 250 0 0 0 30 0 T45 250 0 70 30 70 0 T47 250 0 100 100100 100 T48 250 0 100 100 100 100 T49 250 20 100 100 100 100 T50 250 0100 100 100 100 T51 250 0 100 100 90 90 T52 250 0 100 100 100 100 T53250 0 100 90 100 90 T54 250 0 100 100 100 100 T55 250 0 60 40 70 0 T56250 0 90 30 80 20 T57 250 0 100 100 100 90 T58 250 0 100 90 100 80 T59250 0 30 30 70 0 T60 250 0 90 50 90 40 T61 250 0 90 90 100 70 T62 250 0100 100 100 100 T63 250 0 100 80 100 90 T64 250 0 100 20 100 60 T65 2500 100 90 100 70 T66 250 0 80 70 90 40 T67 250 0 70 0 90 0 T68 250 0 70 080 0 T69 250 0 90 60 100 40 T70 250 0 90 70 90 10 T71 250 0 90 20 90 40P3 250 0 90 50 90 30 P4 250 0 90 40 90 0 P5 250 0 0 0 0 0 P6 250 0 100100 100 90 P7 250 0 100 80 100 80 P9 250 30 80 90 100 80

1. Compounds of formula I

wherein R¹, R², R³ and R⁴, independently of each other, are hydrogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxyC₁-C₄ alkyl,C₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄alkylsulfinylC₁-C₄alkyl,C₁-C₂alkylsulfonylC₁-C₄alkyl; C₅-C₇cyclopropyl or cyclopropylsubstituted by C₁- or C₂alkyl, C₁- or C₂haloalkyl or halogen; cyclobutylor cyclobutyl substituted by C₁- or C₂ alkyl; oxetanyl or oxetanylsubstituted by C₁- or C₂ alkyl; C₅-C₇cycloalkyl or C₅-C₇cycloalkylsubstituted by C₁- or C₂alkyl or C₁- or C₂haloalkyl, where a methylenegroup of the cycloalkyl moiety is optionally replaced by an oxygen orsulfur atom or a sulfinyl or sulfonyl group; C₄-C₇cycloalkenyl orC₄-C₇cycloalkenyl substituted by C₁- or C₂alkyl or C₁- or C₂haloalkyl,where a methylene group of the cycloalkenyl moiety is optionallyreplaced by an oxygen or sulfur atom or a sulfinyl or sulfonyl group;cyclopropylC₁-C₅alkyl or cyclopropylC₁-C₅alkyl substituted by C₁- orC₂alkyl, C₁- or C₂haloalkyl or halogen; cyclobutylC₁-C₅alkyl orcyclobutylC₁-C₅alkyl substituted by C₁-C₂ alkyl; oxetanylC₁-C₅alkyl oroxetanylC₁-C₅alkyl substituted by C₁- or C₂alkyl;C₅-C₇cycloalkylC₁-C₅alkyl or C₅-C₇cycloalkylC₁-C₅alkyl substituted byC₁- or C₂alkyl or C- or C₂haloalkyl, where a methylene group of thecycloalkyl moiety is optionally replaced by an oxygen or sulfur atom ora sulfinyl or sulfonyl group; C₄-C₇cycloalkenylC₁-C₅alkyl orC₄-C₇cycloalkenylC₁-C₅alkyl which is substituted by C₁- or C₂alkyl orC₁- or C₂haloalkyl, where a methylene group of the cycloalkenyl moietyis optionally replaced by an oxygen or sulfur atom or a sulfinyl orsulfonyl group; phenyl or phenyl substituted by C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄haloalkyl, halogen, nitro, cyano, C₁-C₄ alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or C₁-C₄alkylcarbonyl; benzyl orbenzyl substituted by C₁-C₄alkyl, C₁-C₄ alkoxy, C₁-C₄haloalkyl, halogen,nitro, cyano, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl orC₁-C₄alkylcarbonyl; heteroaryl or heteroaryl substituted by C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄haloalkyl, halogen, nitro, cyano, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or C₁-C₄alkylcarbonyl; or R¹ andR², or R³ and R⁴, are joined to form a 3-7 membered saturated ring inwhich a methylene group is optionally replaced by an oxygen or sulfuratom, and which may be optionally substituted by C₁- or C₂-alkyl,halogen or C₁-C₂ alkoxy, or a 5-7 membered unsaturated ring in which amethylene group is optionally replaced by an oxygen or sulfur atom, andwhich may be optionally substituted by C₁- or C₂-alkyl, halogen or C₁-C₂alkoxy; or R¹ and R³ are joined to form a 5-7 membered saturated orunsaturated ring or a 5-7 membered saturated or unsaturated ringoptionally substituted by C₁- or C₂alkyl, C₁- or C₂alkoxy, hydroxy orhalogen; Y is O, C═O, S(O)_(m) or S(O)_(n)NR⁵; provided that when Y isC═O, R³ and R⁴ are different from hydrogen when either R¹ or R² ishydrogen, and R¹ and R² are different from hydrogen when either R³ or R⁴is hydrogen; m is 0 or 1 or 2 and n is 0 or 1; R⁵ is hydrogen,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxycarbonyl,tri(C₁-C₆alkyl)silyl-ethyloxycarbonyl, C₁-C₆haloalkoxycarbonyl, cyano,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆cycloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted byR⁶; benzylcarbonyl or benzylcarbonyl substituted by R⁶; pyridylcarbonylor pyridylcarbonyl substituted by R⁶; phenoxycarbonyl or phenoxycarbonylsubstituted by R⁶; benzyloxycarbonyl or benzyloxycarbonyl substituted byR⁶; R⁶ is C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, nitro, cyano, formyl,carboxyl or halogen; Het is a an optionally substituted monocyclic orbicyclic heteroaryl, and G is hydrogen, an alkali metal, alkaline earthmetal, sulfonium, ammonium or a latentiating group.
 2. Compoundsaccording to claim 1, wherein R¹, R², R³ and R⁴, independently of eachother, are hydrogen, C₁-C₄ alkyl.
 3. Compounds according to claim 2,wherein R¹, R², R³ and R⁴, independently of each other, are hydrogen,methyl or ethyl.
 4. Compounds according to claim 3, wherein R¹, R², R³and R⁴ are methyl.
 5. Compounds according to claim 1, wherein R¹ and R³are joined to form a 5-7 membered saturated or unsaturated ring or a 5-7membered saturated or unsaturated ring substituted by C₁- or C₂alkyl,C₁- or C₂alkoxy or halogen and wherein R² and R⁴, independently of eachother, are hydrogen, methyl or ethyl.
 6. Compounds according to claim 1,wherein Y is O, S or C═O.
 7. Compounds according to claim 1, wherein Gis hydrogen, an alkali metal or alkaline earth metal.
 8. Compoundsaccording to claim 7, wherein G is hydrogen.
 9. Compounds according toclaim 1, wherein Het is an optionally substituted monocyclic 5- or6-membered nitrogen or sulfur containing heteroaryl.
 10. Compoundsaccording to claim 9, wherein Het is a group of the formula R₁ to R₁₂

wherein A designates the point of attachment to the ketoenol moiety, andW¹ is N or CR¹⁰; W² and W³ are independently of each other N or CR⁸; W⁴is N or CR¹¹; with the proviso that at least one of W¹, W², W³ or W⁴ isN; X is O, S, Se, or NR¹³; Z is N or CR¹⁴; R⁷ is halogen, C₁-C₄ alkyl,C₃-C₈ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl,C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, nitro or cyano; R⁸ is hydrogen,halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₁-C₄ alkoxy, C₂-C₄alkenyloxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulphinyl, C₁-C₄ alkylsulphonyl,C₁-C₄ alkoxy C₁-C₄ alkyl, poly C₁-C₄ alkoxyC₁-C₄ alkyl, C₁-C₄ alkylthioC₁-C₄ alkyl, each of which is unsubstituted or substituted by halogen,C₃-C₈cycloalkyl, thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl,isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl,pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazolyl, thiadiazolyl,pyridazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl andquinoxalinyl, N-oxides and salts thereof, each of these substituentsbeing unsubstituted or substituted by halogen, C₁-C₄ alkyl, haloC₁-C₄alkyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy, C₁-C₄ alkylthio, C₁-C₄alkylsulphinyl, C₁-C₄ alkyl-sulphonyl, haloC₁-C₄ alkyl, haloC₁-C₄alkoxy, cyano or nitro; R⁹ is hydrogen, C₁-C₄ alkyl, C₂-C₃alkenyl,C₂-C₃alkynyl, C₁-C₄ haloalkyl or C₂-C₃ haloalkenyl; R¹⁰ is hydrogen,methyl, halomethyl or halogen; R¹¹ is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl or cyano; R¹² is hydrogen, methyl, ethyl, halomethyl,haloethyl, aryl, aryl substituted by C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂haloalkyl, C₁-C₂ haloalkoxy, cyano or nitro, heteroaryl or heteroarylsubstituted by C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂haloalkoxy, cyano or nitro; R¹³ is hydrogen, methyl or halomethyl; andR¹⁴ is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano ornitro.
 11. Compounds according to claim 10, wherein Het is a group ofthe formula R₂, wherein X is sulfur, R⁸ is thienyl, furyl, pyrrolyl,isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl,triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl,oxadiazolyl, thiadiazolyl, pyridazinyl, quinolinyl, isoquinolinyl,cinnolinyl, quinazolinyl and quinoxalinyl, N-oxides and salts thereof,each of which is optionally substituted one to three times by halogen,C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy, cyano ornitro, and Z is nitrogen or C—H.
 12. Compounds according to claim 10,wherein Het is a group of the formula R₂, wherein X is sulfur, R⁷ ismethyl or ethyl, R⁸ is phenyl, phenyl substituted one to three times byhalogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂ haloalkyl, C₁-C₂ haloalkoxy,cyano or nitro, and Z is nitrogen or C—H.
 13. (canceled)
 14. A processfor the preparation of a compound of the formula I according to claim 1,wherein in the compound of the formula I Het is a group of formula (R₂)and Y, R¹, R², R³ and R⁴ are as defined in claim 1, R⁸ is hydrogen,halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₁-C₄ alkoxy, C₂-C₄alkenyloxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulphinyl, C₁-C₄ alkylsulphonyl,C₁-C₄ alkoxy C₁-C₄ alkyl, poly C₁-C₄ alkoxyC₁-C₄ alkyl, C₁-C₄ alkylthioC₁-C₄ alkyl, each of which is unsubstituted or substituted by halogen,C₃-C₈cycloalkyl, thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl,isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl,pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazolyl, thiadiazolyl,pyridazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl andquinoxalinyl, N-oxides and salts thereof, each of these substituentsbeing unsubstituted or substituted by halogen, C₁-C₄ alkyl, haloC₁-C₄alkyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy, C₁-C₄ alkylthio, C₁-C₄alkylsulphinyl, C₁-C₄ alkyl-sulphonyl, haloC₁-C₄ alkyl, haloC₁-C₄alkoxy, cyano or nitro, and R″ is hydrogen, alkyl or haloalkyl, by therearrangement of a compound of formula (R)


15. A process for the preparation of a compound of the formula Iaccording to claim 1, wherein in the compound of the formula I Het is agroup of formula R₃ and Y, R¹, R², R³ and R⁴ are as defined in claim 1,R⁸ is hydrogen, halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₁-C₄alkoxy, C₂-C₄ alkenyloxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulphinyl, C₁-C₄alkylsulphonyl, C₁-C₄ alkoxy C₁-C₄ alkyl, poly C₁-C₄ alkoxyC₁-C₄ alkyl,C₁-C₄ alkylthio C₁-C₄ alkyl, each of which is unsubstituted orsubstituted by halogen, C₃-C₈cycloalkyl, thienyl, furyl, pyrrolyl,isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl,triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl,oxadiazolyl, thiadiazolyl, pyridazinyl, quinolinyl, isoquinolinyl,cinnolinyl, quinazolinyl and quinoxalinyl, N-oxides and salts thereof,each of these substituents being unsubstituted or substituted byhalogen, C₁-C₄ alkyl, haloC₁-C₄ alkyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy,C₁-C₄alkylthio, C₁-C₄alkylsulphinyl, C₁-C₄ alkyl-sulphonyl, haloC₁-C₄alkyl, haloC₁-C₄ alkoxy, cyano or nitro, and R″ is hydrogen, alkyl orhaloalkyl, by the rearrangement of a compound of formula (T)


16. A process for the preparation of a compound of the formula Iaccording to claim 1, wherein in the compound of the formula I G ishydrogen, which comprises cyclisation of the compound of the formula (B)

wherein Het, R¹, R², R³, R⁴ and Y have the meanings assigned to them inclaim 1 and R is hydrogen, under acidic conditions.
 17. A process forthe preparation of a compound of the formula I according to claim 1,wherein in the compound of the formula I G is hydrogen, which comprisescyclisation of the compound of the formula (B)

wherein Het, R¹, R², R³, R⁴ and Y have the meanings assigned to them inclaim 1 and R is alkyl, under basic conditions.
 18. Compounds of theformulae (R) and (T)

wherein R″ is hydrogen, C₁-C₄ alkyl or C₁-C₄ haloalkyl, R¹, R², R³ andR⁴, independently of each other, are hydrogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxyC₁-C₄ alkyl, C₁-C₄alkylthioC₁-C₄alkyl,C₁-C₄alkylsulfinylC₁-C₄alkylsulfonylC₁-C₄alkyl, cyclopropyl orcyclopropyl substituted by C₁- or C₂alkyl, C₁- or C₂ halogen; cyclobutylor cyclobutyl substituted by C₁- or C₂ alkyl; oxetanyl or oxetanylsubstituted by C₁- or C₂ alkyl; C₅-C₇cycloalkyl or C₅-C₇cycloalkylsubstituted by C₁- or C₂alkyl or C₁- or C₂haloalkyl, where a methylenegroup of the cycloalkyl moiety is optionally replaced by an oxygen orsulfur atom or a sulfinyl or sulfonyl group; C₄-C₇cycloalkenyl orC₄-C₇cycloalkenyl substituted by C₁- or C₂alkyl or C₁- or C₂haloalkylwhere a methylene group of the cycloalkenyl moiety is optionallyreplaced by an oxygen or sulfur atom or a sulfinyl or sulfonyl group;cyclopropylC₁-C₅alkyl or substituted by C₁- or C₂alkyl, C₁- orC₂haloalkyl or halogen; cyclobutylC₁-C₅alkyl or cyclobutylC₁-C₅alkylsubstituted by C₁-C₂ alkyl; oxetanylC₁-C₅alkyl or oxetanylC₁-C₅alkylsubstituted by C₁- or C₂alkyl; C₅-C₇cycloalkylC₁-C₅alkyl orC₅-C₇cycloalkylC₁-C₅alkyl substituted by C₁- or C₂alkyl or C₁- orC₂haloalkyl, where a methylene group of the moiety is optionallyreplaced by an oxygen or sulfur atom or a sulfinyl or sulfonyl group;C₄-C₇cycloalkenylC₁-C₅alkyl or C₄-C₇cycloalkenylC₁-C₅alkyl which issubstituted by C₁- or C₂alkyl or C₁- or C₂haloalkyl, ere a methylenegroup of the cycloalkenyl moiety is optionally replaced by an oxygen orsulfur atom or a sulfinyl or sulfonyl group; phenyl or phenylsubstituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl, halogen, nitro,cyano, C₁-C₄ alkylthio, C₁-C₄alkylsulfonyl or C₁-C₄alkylsulfonyl orC₁-C₄alkylcarbonyl; benzyl or benzyl substituted by C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄haloalkyl, halogen, nitro, cyano, C₁-C₄ alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or C₁-C₄alkylcarbonyl; heteroarylor heteroaryl substituted by C₁-C₄alkyl C₁-C₄alkoxy, C₁-C₄haloalkyl,halogen, nitro, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl or C₁-C₄alkylcarbonyl; or R¹ and R² or R³ and R⁴, arejoined to form a 3-7 membered saturated ring in which a methylene groupis optionally replaced by an oxygen or sulfur atom, and which may beoptionally substituted by C₁- or C₂-alkyl, halogen or C₁-C₂ alkoxy, or a5-7 membered ring unsaturated ring in which a methylene group isoptionally replaced by an oxygen or sulfur atom, and which may beoptionally substituted by C₁- or C₂-alkyl, halogen or C₁-C₂ alkoxy; orR¹ and R³ are joined to form a 5-7 membered saturated or unsaturatedring or a 5-7 membered saturated or unsaturated ring optionallysubstituted by C₁- or C₂alkyl, C₁- or C₂alkoxy, hydroxy or halogen; Y isO, C═O, S(O)_(m) or S(O)_(n)NR⁵; provided that when Y is C═O, R³ and R⁴are different from hydrogen when either R¹ or R² is hydrogen, and R¹ andR² are different from hydrogen when either R³ or R⁴ is hydrogen; m is 0or 1 or 2 and n is 0 or 1; R⁵ is hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆alkoxycarbonyl, tri(C₁-C₆alkyl)silyl-ethyloxycarbonyl,C₁-C₆haloalkoxycarbonyl, cyano, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl,C₁-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆haloalkenyl, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₁-C₆cycloalkylcarbonyl, phenylcarbonyl orphenylcarbonyl substituted by R⁶; benzylcarbonyl or benzylcarbonylsubstituted by R⁶; pyridylcarbonyl or pyridylcarbonyl substituted by R⁶;phenoxycarbonyl or phenoxycarbonyl substituted by R⁶; benzyloxycarbonylor benzyloxycarbonyl substituted by R⁶; R⁶ is C₁-C₆haloalkyl,C₁-C₆alkoxycarbonyl, nitro, cyano, formyl, carboxyl halogen; X is O, S,Se, or NR¹³; Z is N or CR¹⁴; R⁸ is hydrogen, halogen, cyano, nitro,C₁-C₄ alkyl, C₂-C₄ alkenyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy, C₁-C₄alkylthio, C₁-C₄ alkylsulphinyl, C₁-C₄ alkylsulphonyl, C₁-C₄ alkoxyC₁-C₄ alkyl, poly C₁-C₄ alkoxyC₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl,each of which is unsubstituted or substituted by halogen,C₃-C₈cycloalkyl, thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl,isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl,pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazolyl, thiadiazolyl,pyridazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl andquinoxalinyl, N-oxides and salts thereof, each of these substituentsbeing unsubstituted or substituted by halogen, C₁-C₄ alkyl, haloC₁-C₄alkyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy, C₁-C₄ alkylthio, C₁-C₄alkylsulphinyl, C₁-C₄ alkyl-sulphonyl, haloC₁-C₄ alkyl, haloC₁-C₄alkoxy, cyano or nitro; R¹³ is hydrogen, methyl or halomethyl; and R¹⁴is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano ornitro.
 19. A method of controlling grasses and weeds in crops of usefulplants, which comprises applying a herbicidally effective amount of acompound of formula I according to claim 1, or of a compositioncomprising such a compound, to the plants or to the locus thereof.
 20. Aherbicidal composition, which, in addition to comprising formulationadjuvants, comprises a herbicidally effective amount of a compound offormula I according to claim
 1. 21. A composition according to claim 20,which, in addition to comprising the compound of formula I, comprises afurther herbicide as mixing partner.
 22. A composition according toclaim 20, which, in addition to comprising the compound of formula I,comprises a safener.
 23. A composition according to claim 20, which, inaddition to comprising the compound of formula I, comprises a furtherherbicide as mixing partner and a safener.